Methyl 4-aminobenzoate → HCID 178498131, compound
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>C(O)C>[F:12][C:13]1[CH:20]=[CH:19][C:16](/[CH:17]=[N:1]/[C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of methyl 4-aminobenzoate (4.57 g, 30.2 mmol) and 4-fluoro-3-nitrobenzaldehyde (5.00 g, 29.6 mmol) in ethanol (30 mL) was stirred at room temperature for 16 hours (precipitates formed within 30 min). The solid product was collected by filtration and the trace amount of solvent was removed under vacuum. 8.32 g (83%) of (E)-methyl 4-(4-fluoro-3-nitrobenzylideneamino)benzoate was obtained as a yellow solid.