Allyl bromide → HCID 19390564, compound

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=[O:13])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[CH2:23]([O:13][C:12]([C:4]1[CH:3]=[C:2]([NH2:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:14])[CH:22]=[CH2:21]

Participants

Procedure

4-Amino-2-quinoline carboxylic acid (800 mg, 4.2 mmol) in DMF (10 ml) and K2CO3 (1.17 g, 8.5 mmol) was stirred at ambient temperature in the presence of allyl bromide (1.47 ml, 17 mmol) for 24 hours. The solvent was evaporated and the crude residue purified by subjecting to silico-gel chromatography, eluting with petroleum ether ethyl acetate 1/1) to give 2-allyloxycarbonyl-4-amino-quinoline (170 mg, NMR (CDCls): δ4.75-5 (m, 4H); 5.2-5.0 (m, 2H); 5.9-6.35 (m, 1H); 7.35-8.3 (m, 5H).