Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinoline
Reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH2:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:24])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 7-benzyloxy-6-methoxy-4-quinolone (9.72 g 34.5 mmol) and phosphorus oxychloride (130 ml) was stirred at 110° C. for 3 hours. The stirred mixture was concentrated at atmospheric pressure. The residue was dissolved in chloroform (150 ml), then ice and water was added to the solution. The mixture was rendered weakly alkaline by the addition of saturated sodium carbonate solution. The two phases were separated, the aqueous layer was extracted with chloroform. The extract was washed with water, dried over sodium sulfate, and the solvent was removed by evaporation under the reduced pressure. The residue was solidified under diisopropyl ether to give 9.82 g of product [E]. Yield: 94%.
Workup
- concentrationThe stirred mixture was concentrated at atmospheric pressure
- dissolutionThe residue was dissolved in chloroform (150 ml)
- additionice and water was added to the solution
- additionby the addition of saturated sodium carbonate solution
- customThe two phases were separated
- extractionthe aqueous layer was extracted with chloroform
- washThe extract was washed with water
- dry with materialdried over sodium sulfate
- customthe solvent was removed by evaporation under the reduced pressure
Sources & evidence
- ORD record
- ord-9432f2c8aead42e5a9fe687ca19655ef
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685971B2
Reaction notes
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