Ammonium formate → Ethyl 8-aminoquinoline-3-carboxylate

Reaction equation

C([O-])=O.[NH4+].Cl[C:6]1[C:15]2[C:10](=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>[Pd].C(O)C>[CH2:22]([O:21][C:19]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:6]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[O:20])[CH3:23]

Participants

Procedure

Ammonium formate was added to a vigorously stirred mixture of 4-chloro-3-ethoxycarbonyl-8-nitro-quinoline (5.6 g), ethanol (1000 ml) and 10% palladium on carbon catalyst (2 g). The mixture was stirred at ambient temperature for 1 hour, filtered through a pad of celite and the pad washed with dichloromethane. The combined filtrate and washings were evaporated to dryness. The residue so obtained was purified by flash chromatography on silica using chloroform as eluant to give 3-ethoxycarbonyl-8-amino-quinoline in 58% yield, mp 94-96° C.