Water → HCID 22643167, compound

Reaction equation

[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[N:7]=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[CH:5]=1)=[N+]=[N-].O>C(OCC)(=O)C.C(O)C>[F:23][C:19]1[CH:18]=[C:17]([C:6]2[CH:5]=[C:4]([NH2:1])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=3)[N:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

Procedure

Into a 500 mL three-neck flask equipped with a condenser, magnetic stirrer, nitrogen inlet gas outlet and a silicone oil heating bath was placed 4-azido-2-(3-fluorophenyl)-6-nitro-quinoline. The material was suspended in 250 mL of ethyl acetate and 50 mL of ethanol. The stirred mixture was heated to reflux, then 20 g (89 mmoles, 6 equiv.) of stannous chloride dihydrate was cautiously added portionwise over 40 min. The reaction was then heated for an additional 2 hr. At the end of this time, the reaction was cooled and then poured into 500 mL of water. The pH was cautiously adjusted to 9.0 and the solution filtered. The solids were washed with 100 mL of ethyl acetate, the filtrates combined and the aqueous layer extracted twice with 200 mL of ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The product was chromatographed on a silica gel column, using 10% methanol in ethyl acetate as eluent, and was then recrystallised from methylene chloride and hexane to give 3.6 g (88%) of the product.