Diisopropylamine → 6-(Benzyloxy)-4-chloro-7-methoxyquinoline
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH2:13][C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.P(Cl)(Cl)([Cl:31])=O>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[Cl:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 110 °C
Procedure
6-Benzyloxy-7-methoxy-4-quinolone (2.4 g), diisopropylamine (5 eq, 7.4 ml), and phosphorus oxychloride (2.5 eq, 2.0 ml) were added, and the mixture was stirred at 110° C. for one hr. The stirred mixture was concentrated under the reduced pressure. Chloroform and iced water were then added to the concentrate. The mixture was rendered weakly alkaline by the addition of 28% aqueous ammonia, followed by extraction with chloroform. The extract was washed with saturated brine and was dried over sodium sulfate, and the solvent was then removed by evaporation under the reduced pressure. The crude thus obtained was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (1.6 g, yield 63%).
Workup
- concentrationThe stirred mixture was concentrated under the reduced pressure
- additionChloroform and iced water were then added to the concentrate
- additionby the addition of 28% aqueous ammonia
- extractionfollowed by extraction with chloroform
- washThe extract was washed with saturated brine
- dry with materialwas dried over sodium sulfate
- customthe solvent was then removed by evaporation under the reduced pressure
- customThe crude thus obtained
- customwas purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-525853d5f91a45e9b8fbf232c9a5801d
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495104B2
Reaction notes
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