Acetic Anhydride → 1-Acetyl-6-hydroxymethyl-1,2,3,4-tetrahydroquinoline
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>CO>[C:13]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][OH:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1)(=[O:15])[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-hydroxymethyl-1,2,3,4-tetrahydroquinoline (314 mg) in methanol (4 ml) was dropwise added acetic anhydride (589 mg) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature. The solvent was removed in vacuo, and ethyl acetate and saturated sodium bicarbonate solution were added to the residue. The organic layer was washed with water and brine, dried and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:2, v/v) to give 1-acetyl-6-hydroxymethyl-1,2,3,4-tetrahydroquinoline (227 mg).