Treatment of N,N-diacetyl-o-toluidine with N-bromosuccinilllide followed by hydrolysis of the intermediate dibromo compound gave o-acetanlinobenzalde-hyde. The reaction was applied successfully to N,N-diacetyl-p-toluidine, N,N-diacetyl-4-chloro-o-toluidine, 2,4-bis(diacetamino)toluene, and 4-acetosy-N,N-diacetyl-o-toluidine. Both o-and p-acetaminobenzaldehyde were required for synthetic work in this laboratory. These compoullds have been prepared in the usual way b y the acetylation (6, 7) of o-and p-aminobenzaldehyde. However, the methods described in the literature for the preparation of o-aminobenzaldehyde by the reduction of o-nitrobenzaldehyde with ferrous sulplzate and ammonia (15) and for p-aminobenzaldehyde by the action of sodium polysulphide upon p-nitrotoluene (3) are tedious, and the products must be used immediately in order t o avoid self-condensation. A direct preparation of o-and p-acetaminobenzaldehyde was suggested b y the hydrolysis of N,N-diacetyl-p-toluidine (16) using aqueous sodium carbon-I ate which gave a quantitative yield of p-acetotoluidide, and also by the work of Brown and Newbold (2) who used N-bromosuccinimide to oxidize 4-I chloromethylmeco~~in(I) t o 3-formylopianic acid (11). I I CH?CI CHO I I1 We found that treatment of N,N-diacetyl-p-toluidine with two moles of N-bromosucciilimide in carbon tetrachloride, followed by aqueous sodium car-bonate hydrolysis without isolatioil of the intermediate bromo compound, gave p-acetaminobenzaldehyde in 70y0 yield. Similarly, N,N-diacetyl-o-toluidine (16) gave o-acetaminobenzaldehyde in 66% yield. The reaction was iilvestigated further with respect t o certain 4-substituted N,N-diacetyl-o-toluidiiles prepared by proloilged refluxing of the toluidine or its acetyl derivative in acetic anhydride. N,N-Diacet~l-4-chloro-o-toluidine, 2,4-bis(diacetamino)toluene, and 4-acetoxy-N,N-diacet~l-o-toluidine when 1 'Manz~script received Az~gust 29, 1955. Cotztrzbutzon from tibe