Partial Reduction of Dinitroarenes to Nitroanilines with Hydrazine Hydrate

Ayyangar, N. R.; Kalkote, Uttam R.; Lugade, A. G.; Nikrad, P. V.; Sharma, Vasant K.

doi:10.1246/bcsj.56.3159

Cited by 18 publications

(7 citation statements)

References 13 publications

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“…The crude product was chromatographed on silica gel using 2:3 EtOAc-hexane to afford 0.71 g (38%) of methyl 3-amino-5-nitrobenzoate: mp 159-160 "C [lit (7,8) mp 159-160 "C]. To a solution of 2.00 g (9.46 mmol) of methyl 3,5-dinitrobenzoate (6) in 135 mL of acetone, 25 mL of acetic acid, and 25 mL of water at reflux was added 2.17 g (38.9 mmol) of iron in three portions at intervals of 20 min.…”

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confidence: 99%

“…The filtrate was adjusted to pH 8 with sodium carbonate, extracted with EtOAc,2 washed with brine, and dried. The crude product was chromatographed on silica gel using 2:3 EtOAc-hexane to afford 0.71 g (38%) of methyl 3-amino-5-nitrobenzoate: mp 159-160 °C [lit (7,8) mp 159-160 °C].…”

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confidence: 99%

“…The organic layer was washed with brine and dried. The product was chromatographed on silica gel using 2:3 EtOAchexane to afford 1.37 g (84%) of methyl 3-azido-5nitrobenzoate: mp 93-94 °C; IR (KBr) 2114 (N3), 1721 (CO) cm'1; XH NMR (CDC13) 8 4.01 (s, 3, OCH3), 8.01 (dd, J = 1.2, 2.2 Hz, 1, ArH), 8.04 (t, J = 2.2 Hz, 1, ArH), 8.60 (dd, J = 1.2, 2.2 Hz, 1, ArH). Anal.…”

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confidence: 99%

“…The filtrate was concentrated, dissolved in EtOAc, washed with aqueous NaHC03 solution and brine, and dried. The solvent was removed to afford 1.98 g (98%) of 13C that was sufficiently pure to be used in the next reaction: mp 163-164 °C dec; IR (KBr) 2128 (N3), 1809, 1788 (CON), 1743 (C02) cm"1; XH NMR (CDC13) 8 2.96 (s, 4, CH2CH2), 8.07 (dd, J = 2.3 and 1.4 Hz, 1, ArH), 8.17 (t, J = 2.1 Hz, 1, ArH), 8.72 (dd, J = 2.0 and 1.4 Hz, 1, ArH); exact mass spectrum calcd for CnH7N506 305.0396, found 305.0396.…”

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confidence: 99%

“…The crude product was chromatographed on silica gel using 1:1 EtOAc-CHCl3 to afford 3.83 g (66%) of 15: mp 104-106 °C; IR (KBr) 3348 (OH), 1732 (C02Me), 1698 (CON of BOC), 1664 (CON) cm"1; XH NMR (CDC13) 8 1.37 (s, 9, C(CH3)3), 2.41 (t, J = 5.4 Hz, 2, Me02CCH2), 2.93 (d, J = 6.3 Hz, 2, CHCH2), 3.42 (t, J = 5.4 Hz, 2, Me02CCH2CH2), 3.66 (s, 3, OCH3), 5.27 (d, J = 7.2 Hz, 1, CHCH2), 6.58 (t, J = 6.3 Hz, 1, NH), 6.75 and 7.01 (2 d, J = 9 Hz, 4, ArH), 7.68 (br s, 1, OH). Anal.…”

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confidence: 99%

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Photoaffinity heterobifunctional crosslinking reagents based on N-(azidobenzoyl)tyrosines

Imai¹,

Kometani²,

Crocker³

et al. 1990

Bioconjugate Chem.

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New heterobifunctional cross-linking reagents that possessed a photoactive terminus, an electrophilic terminus, and a linking arm between the two termini that had a radiolabeled, enzymatically cleavable bond were synthesized. In a model study, succinimidyl N-[N'-(4-azidobenzoyl)tyrosyl]-beta-alanate (16A) was coupled to n-butylamine (a Lys surrogate), iodinated, and cleaved with chymotrypsin in the presence of tyrosylamide to afford the desired adduct (N-(N'-(4-azidobenzoyl)-3-iodotyrosyl)tyrosinamide, thereby demonstrating the feasibility of the enzymatic cleavage. In a biochemical study, succinimidyl N-[N'-(3-azido-5-nitrobenzoyl)tyrosyl]-beta-alanate (16C) was coupled to Lys-75 of calmodulin (CaM), and the radioiodinated monoadduct was successfully photo-cross-linked, in a calcium-dependent manner, to the human erythrocyte plasma membrane Ca2+,Mg2(+)-ATPase and to a synthetic fragment (M13) containing the CaM-binding region of myosin light-chain kinase. In the latter case, densitometry readings indicated 20% cross-linking efficiency.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Photoaffinity heterobifunctional crosslinking reagents based on N-(azidobenzoyl)tyrosines

Imai¹,

Kometani²,

Crocker³

et al. 1990

Bioconjugate Chem.

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Hydrazine and Its Derivatives

Schiessl

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Hydrazine (diamide), N 2 H 4 , a colorless liquid having an ammoniacal odor, is the simplest diamine and unique in its class because of the N—N bond. Hydrazine and its simple methyl and dimethyl derivatives have endothermic heats of formation and high heats of combustion. Hence these compounds are used as rocket fuels. Other derivatives are used as gas generators and explosives. Hydrazine, a base slightly weaker than ammonia, forms a series of useful salts. As a strong reducing agent, hydrazine is used for corrosion control in boilers and hot‐water heating systems; also for metal plating, reduction of noble‐metal catalysts, and hydrogenation of unsaturated bonds in organic compounds. Hydrazine is also an oxidizing agent under suitable conditions. Having two active nucleophilic nitrogens and four replaceable hydrogens, hydrazine is the starting material for many derivatives, among them foaming agents for plastics, antioxidants, polymers, polymer cross‐linkers and chain‐extenders, as well as fungicides, herbicides, plant‐growth regulators, and pharmaceuticals. Hydrazine is also a good ligand; numerous complexes have been studied. Many heterocyclics are based on hydrazine, where the rings contain from one to four nitrogen atoms as well as other heteroatoms. The many advantageous properties of hydrazine assure continued‐commercial utility. Hydrazine is available in anhydrous form as well as aqueous solutions, typically 35, 51.2, 54.4, and 64 wt % N 2 H 4 (54.7, 80, 85, and 100% hydrazine hydrate). The commercially feasible processes involve partial oxidation of ammonia (or urea) using hypochlorite or hydrogen peroxide. Most hydrazine is produced by some variation of the Raschig process, which is based on the oxidation of ammonia using alkaline hypochlorite. Hydrazine is toxic and readily absorbed by oral, dermal, or inhalation routes of exposure.

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Hydrazine and Its Derivatives

Rothgery¹

2004

Kirk-Othmer Encyclopedia of Chemical Technology

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Hydrazine (diamide), N 2 H 4 , a colorless liquid having an ammoniacal odor, is the simplest diamine and unique in its class because of the NN bond. Hydrazine and its simple methyl and dimethyl derivatives have endothermic heats of formation and high heats of combustion. Hence, these compounds are used as rocket fuels. Other derivatives are used as gas generators and explosives. Hydrazine, a base slightly weaker than ammonia, forms a series of useful salts. As a strong reducing agent, hydrazine is used for corrosion control in boilers and hot‐water heating systems; also for metal plating, reduction of noble‐metal catalysts, and hydrogenation of unsaturated bonds in organic compounds. Hydrazine is also an oxidizing agent under suitable conditions. Having two active nucleophilic nitrogens and four replaceable hydrogens, hydrazine is the starting material for many derivatives, among them foaming agents for plastics, antioxidants, polymers, polymer cross‐linkers and chain‐extenders, as well as fungicides, herbicides, plant‐growth regulators, and pharmaceuticals. Hydrazine is also a good ligand; numerous complexes have been studied. Many heterocyclics are based on hydrazine, where the rings contain from one to four nitrogen atoms as well as other heteroatoms. The many advantageous properties of hydrazine assure continued‐commercial utility. Hydrazine is available in anhydrous form as well as aqueous solutions, typically 35, 51.2, 54.4, and 64 wt % N 2 H 4 (54.7, 80, 85, and 100% hydrazine hydrate). The commercially feasible processes involve partial oxidation of ammonia (or urea) using hypochlorite or hydrogen peroxide. Most hydrazine is produced by some variation of the Raschig process, which is based on the oxidation of ammonia using alkaline hypochlorite. Hydrazine is toxic and readily absorbed by oral, dermal, or inhalation routes of exposure.

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Partial Reduction of Dinitroarenes to Nitroanilines with Hydrazine Hydrate

Cited by 18 publications

References 13 publications

Photoaffinity heterobifunctional crosslinking reagents based on N-(azidobenzoyl)tyrosines

Photoaffinity heterobifunctional crosslinking reagents based on N-(azidobenzoyl)tyrosines

Hydrazine and Its Derivatives

Hydrazine and Its Derivatives

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