N,N-Dimethylaniline → 6-Allyl-5-hydroxy-3,8-dimethylcarbostyril
Reaction equation
CN(C)[C:3]1[CH:8]=CC=C[CH:4]=1.C([O:13][C:14]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]2[C:15]=1[CH:16]=[C:17]([CH3:26])[C:18](=[O:25])[NH:19]2)C=C>CCCCCC>[CH2:8]([C:23]1[C:14]([OH:13])=[C:15]2[C:20](=[C:21]([CH3:24])[CH:22]=1)[NH:19][C:18](=[O:25])[C:17]([CH3:26])=[CH:16]2)[CH:3]=[CH2:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
N,N-dimethylaniline (10 ml) was added to 5-allyloxy-3,8-dimethylcarbostyril (4.32 g, 18.9 mmol), and stirred for 2 hours and 40 minutes in a bath of 200° C. in the atmosphere of argon. After cooling, hexane was added. Precipitated crystals were collected by filtration, and purified by silica gel chromatography (chloroform:methanol =10:1). The purified product was subjected to recrystallization (chloroform-n-hexane) to obtain 3.86 g of the title compound as colorless crystals (89.4%).