Phosphorus oxychloride → 1-(2-Methyl-4-benzyloxyphenyl)-4-[(2-hydroxyethyl)amino]-6-beta,beta,beta-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[C:22]=3[NH:21][C:20](=O)[C:19]=2[CH2:18][CH2:17]1.P(Cl)(Cl)(Cl)=O>>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([O:29][CH2:30][C:31]([F:32])([F:33])[F:34])[C:22]=3[N:21]=[C:20]([NH:21][CH2:22][CH2:23][OH:29])[C:19]=2[CH2:18][CH2:17]1Participants
3
Reactant 2
Product 1
Conditions
- Temperature
- 110 °C
Procedure
1-(2-Methyl-4-benzyloxyphenyl)-4-oxo-6-β,β,β-trifluoroethoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline(2.7 g, 5.6 mmol) was mixed with phosphoryl chloride(15 ml), and stirred at 110° C. for 30 minutes. After removing the excess phosphoryl chloride by distillation, the residue was dissolved in dichloromethane (50 ml), neutralized with aqueous solution of sodium bicarbonate, and stirred at room temperature for 30 minutes. The reaction mixture was extracted with dichloromethane, and the organic layer was washed with water for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography(ethyl acetate:hexane=1:10) to obtain 1.7 g of desired compound as solid in 60% of yield.