Methylamine → 4-Fluoro-2-methyl-7-nitroisoindolin-1-one
Reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([F:13])[C:5]=1[CH2:14]Br.[CH3:17][NH2:18]>C1COCC1>[F:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]2[C:5]=1[CH2:14][N:18]([CH3:17])[C:3]2=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
At room temperature, a solution of 2-bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester (4.48 g, 15.3 mmol) in THF (100 mL) is treated with 2M solution of methylamine in THF (23 mL, 46 mmol), and the mixture is stirred for 48 h at the room temperature. The reaction mixture is filtrated through a glass filter and the precipitates are collected and washed with ethyl acetate. The filtrate is washed with sat. aqueous solution of NaHCO3 and brine, dried over Na2SO4, and concentrated under reduced pressure to give 4-fluoro-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (1.6 g, 7.61 mmol 50%) as yellow solids. 1H-NMR (400 MHz, δ, ppm) CDCl3: 3.22 (s, 3H), 4.47 (s, 2H), 7.32 (dd, 1H), 7.84 (dd, 1H).