Methanol → (2-amino-4-fluorophenyl)-N-(1-methylethyl)-methylamine

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH:13]([NH2:16])([CH3:15])[CH3:14].[CH3:17]O>[Pd]>[NH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[N:16]([CH3:17])[CH:13]([CH3:15])[CH3:14]

Participants

Procedure

To a solution of 4-fluoro-2-nitro benzaldehyde (3.76 g, 25 mmol) in dry MeOH (120 ml), was added isopropyl amine (2.1 ml, 25 mmol) and the mixture stirred for 2 hours at room temperature in Argon atmosphere. Then it was then transferred into a Parr bottle containing 5% Pd on charcoal (246 mg) under Argon and hydrogenated at 30 psi for 18 hours. The suspension was filtered over a celite pad, washed with MeOH and evaporated at reduced pressure to afford (2-amino-4-fluorophenyl)-N-(1-methylethyl)-methylamine as a yellow oil.