Ammonia → 3-Carbamoyl-4-chloro-8-nitroquinoline

Reaction equation

[C:1]([CH:4]1[C:13](=O)[C:12]2[C:7](=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5]1)(O)=[O:2].S(Cl)([Cl:20])=O.[NH3:22]>>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[Cl:20])=[CH:11][CH:10]=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])(=[O:2])[NH2:22]

Participants

Reactant 3

HCID 222Ammonia

HCID 24386Thionyl Chloride

HCID 212500243-Carboxy-8-nitro-4-oxo-3,4-dihydroquinoline

Product 1

HCID 212501013-Carbamoyl-4-chloro-8-nitroquinolineYield 79%

Procedure

Using an analogous procedure to that described in Example 2, in the section relating to the preparation of starting materials, 3-carboxy-8-nitro-4-oxo-3,4-dihydroquinoline was reacted with thionyl chloride and then concentrated aqueous ammonia. The product so obtained was recrystallised from ethanol to give 3-carbamoyl-4-chloro-8-nitroquinoline in 79% yield, mp 277-279° C.