Methylhydrazine → 4-Aminooxymethyl-2-bromo-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][N:13]2C(=O)C3C(=CC=CC=3)C2)=O)=[CH:6][C:5]=1[Br:23].CNN>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:12][NH2:13])=[CH:6][C:5]=1[Br:23]Participants
4
Procedure
To a solution of 2-bromo-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-benzoic acid methyl ester (0.40 g, 1.02 mmol) in methylene chloride (15 mL) cooled to 0° C. was added methyl hydrazine (0.087 g, 1.88 mmol). After a few minutes the ice bath was removed and the mixture was allowed to stir at room temperature for 2 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using ethyl acetate/methylene chloride (0/100 gradient to 6/94) to give 4-aminooxymethyl-2-bromo-benzoic acid methyl ester (0.25 g, 94%) as a colorless oil. 1H NMR (400 MHz, CDCl3); δ 7.79 (d, 1H), 7.66 (s, 1H), 7.32 (d, 1H), 4.67 (s, 2H), 3.92 (s, 3H).