2-Chloro-6-nitrobenzaldehyde → 2-Chloro-6-nitrobenzylideneaminooxyacetic Acid

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=O.[ClH:13].[C:14]([CH2:17][O:18][NH2:19])([OH:16])=[O:15].C(CON)(O)=O.C([O-])(=O)C.[Na+]>O>[Cl:13][CH:17]([O:18][N:19]=[CH:4][C:3]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][CH:2]=1)[C:14]([OH:16])=[O:15]

Participants

Procedure

A warm solution of 2.5 gm. (0.014 mole) of 2-chloro-6-nitrobenzaldehyde in 40 ml. of alcohol 3A was added, with stirring, to a warm solution of 1.5 gm. (0.014 equivs.) of carboxymethoxylamine hemihydrochloride and 1.7 gm. (0.021 equiv.) of anhyd. sodium acetate in 40 ml. of water. The reaction mixture was heated a half-hour on the steam bath, and was then evaporated to a volume of about 20 ml. A solid separated upon cooling; it was filtered from the mixture, washed with cold water and dried in air to give 2.7 gm. (77.3%) of tan-yellow colored material melting at 136°-141° C. Recrystallization from n-hexane/isopropyl alcohol yield 2.5 gm. of pale tan-yellow crystalline product melting at 144°-146° C.