Formation of 3-Aminophenols from Cyclohexane-1,3-diones

Szymor-Pietrzak, Damian; Khan, Muhammad Naseem; Kumar, Ajay; Depner, Noah; Clive, Derrick L. J.

doi:10.1021/acs.joc.0c02284

Cited by 6 publications

(7 citation statements)

References 56 publications

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“…According to the literature, 13b 1,3-cyclohexadione 6a (5.0 g, 39.7 mmol), methanol (8 mL, 198 According to the literature, 19 1,3-cyclohexadione 6a (100 mg, 0.89 mmol) was dissolved in AcOH (1 mL), and NH2Me (0.76 mL, 2M in THF, 1.52 mmol) was added. The reaction was sealed and stirred at 90 ℃ for 33 h. The solvent was evaporated, Flash chromatography of the residue over silica gel using DCM/MeOH (30:1, v/v) gave 6c (91 mg, 82%) as a yellow amorphous powder.…”

Section: -Methoxycyclohex-2-en-1-one (6b)mentioning

confidence: 99%

A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Chen

Xie

et al. 2022

Synthesis

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We represented herein a two-step synthesis of 1-methyl-6H-indol-6-one (1) which is an N-containing 6/5 fused bicyclic building blocks in Amaryllidaceae alkaloids. The key step featured with a “one-pot” ozonolysis/reductive amination/cyclization of allylated 1,3-cyclohexadione (6) to give bicyclic compounds (1). Moreover, the formal total synthesis of natural product γ-lycorane could be achieved through a photo-promoted cyclization/oxidation cascade reaction from the resulting bicyclic intermediate 1h.

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Section: -Methoxycyclohex-2-en-1-one (6b)mentioning

confidence: 99%

A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Chen

Xie

et al. 2022

Synthesis

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“…Thus, the positive effect of AcOH as a solvent was confirmed. 13 Further experimentation revealed that the concentration of the reactant solution could be increased to 2.0 M from 0.2 M and the residence time could be shortened to 5 minutes from 30 minutes (Table 1, entry 10). 14 With this change, the processing rate of N -methylaniline ( 9 ) increased 60 times from 0.13 to 7.8 mL per hour.…”

Section: Resultsmentioning

confidence: 99%

Multi-platform synthesis of ondansetron featuring process intensification in flow

Hato

Jamison

2023

React. Chem. Eng.

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“…3-Aminophenol (empirical formula C 6 H 7 NO, CAS No. 591–27–5, shown in Figure ) is a pharmaceutical intermediate . It is a white crystalline powder.…”

Section: Introductionmentioning

confidence: 99%

“…591− 27−5, shown in Figure 1) is a pharmaceutical intermediate. 1 It is a white crystalline powder. 3-Aminophenol, an intermediate, is widely used in pesticides, medicines, dyes, the petrochemistry industry, and other fields.…”

Section: Introductionmentioning

confidence: 99%

Solubility Determination, Modeling, and Thermodynamic Analysis of 3-Aminophenol in Ten Monosolvents and Three Binary Mixed Solvents

Wu,

Xue,

Wang

et al. 2024

J. Chem. Eng. Data

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The solubilities of 3-aminophenol in monosolvents (ethyl acetate, isopropyl acetate, n-butyl acetate, amyl acetate, 1,2-dichloroethane, trichloromethane, benzene, 1,4-dioxane, tetrahydrofuran, and acetonitrile) and binary solvent mixtures (1,4-dioxane + water, tetrahydrofuran + water, and acetonitrile + water) were determined by a static gravimetric method at temperatures ranging from 283.15 to 328.15 K under atmospheric pressure. The solubility of 3-aminophenol in all solvent systems is positively correlated with temperature. In monosolvents, the solubility order of 3-aminophenol was as follows: THF > 1,4-dioxane > acetonitrile > ethyl acetate > isopropyl acetate > n-butyl acetate > amyl acetate > 1,2-dichloroethane > trichloromethane > benzene. The maximum solubility value occurred in 1,4-dioxane (x 1 = 0.3700 mol·mol–1, T = 328.15 K), and the minimum solubility value occurred in benzene (x 1 = 0.0005505 mol·mol–1, T = 288.15 K). In general, the solubility of 3-aminophenol in 1,4-dioxane + water and THF + water is greater than that in acetonitrile + water. There is a cosolvency phenomenon of 3-aminophenol in the solvents of 1,4-dioxane + water and acetonitrile + water. The experimental solubility data were correlated by the modified Apelblat model, the Yaws model, the λh model, the Sun model, the modified Jouyban–Acree model, and the Wilson model. The modified Apelblat model best fitted the experimental data among all of the selected models in monosolvents (with relative average deviation (RAD) and root-mean-square deviation (RMSD) less than 0.0156 and 0.001212, respectively) and binary solvent mixtures (with RAD and RMSD less than 0.0102 and 0.001408, respectively). Based on the experimental data of the solubility of 3-aminophenol in mono and binary solvents, the Wilson model was used to calculate the dissolution properties (Δdis H, Δdis S, and Δdis G). The results indicate that the dissolution process of 3-aminophenol is endothermic, entropy-increasing, and spontaneous. All of the selected models for both mono and binary solvents provide satisfactory correlation results.

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Formation of 3-Aminophenols from Cyclohexane-1,3-diones

Cited by 6 publications

References 56 publications

A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Multi-platform synthesis of ondansetron featuring process intensification in flow

Solubility Determination, Modeling, and Thermodynamic Analysis of 3-Aminophenol in Ten Monosolvents and Three Binary Mixed Solvents

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