Methylamine → 1-Amino-2-(2-fluorobenzoyl)pyrrole

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[N:7]([N:11]2C(=O)C3=CC=CC=C3C2=O)[CH:8]=[CH:9][CH:10]=1)=[O:5].CN>CN(C=O)C.O>[NH2:11][N:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[C:3]1[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=1[F:1]

Participants

Procedure

To a suspension of 2-(2-fluorobenzoyl)-1-phthalimidopyrrole (12.5 g, 27 mmole) in 40 ml DMF was added 40 ml methylamine (40% solution in water). After stirring one hour at ambient temperature, the reaction mixture was diluted with water and extracted with ether. The organic extract was washed with water and with saturated NaCl solution, dried over anhydrous MgSO4, filtered and evaporated to 9 g oil, half of which was purified by Kugelrohr distallation (120°-130° at 0.2 mm Hg) to give 3.5 g (93%) solid, m.p. 44°-47°.