Ammonia → N-(4-chloro-2-methyl-6-quinolyl)acetamide
Reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[C:4]([CH3:16])[CH:3]=1.P(Cl)(Cl)([Cl:19])=O.N>>[Cl:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[C:4]([CH3:16])[CH:3]=1Participants
4
Procedure
N-(4-Hydroxy-2-methyl-6-quinolyl)acetamide (4.32 g, 20 mmol) and phosphorus oxychloride (9.32 ml, 100 mmol) were heated at 100° C. for 15 min. The reaction mixture was cooled to room temperature and poured into ice water. Thereto was added 28% aqueous ammonia to make the solution alkaline. The resulting insoluble matter was collected by filtration, washed with ether and water, dried under reduced pressure at 80° C. to give N-(4-chloro-2-methyl-6-quinolyl)acetamide (6.85 g, crude, yellow solid).