Aluminium lithium hydride → 7-Chloro-1-(3-hydroxypropyl)imidazo[1,5-a]quinoxalin-4(5H)-one
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([CH2:15][CH2:16][C:17](OCC)=[O:18])=[N:13][CH:14]=[C:7]1[C:6](=[O:22])[NH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[N:13][CH:14]=[C:7]1[C:6](=[O:22])[NH:5]2Participants
4
Procedure
Fifty (50) mg of ethyl 3-(7-chloro-4-oxo-4,5-dihydroimidazo-[1,5-a]quinoxalin-1-yl)propanoate as synthesized in Example 176 was dissolved in 5 mL of tetrahydrofuran, and to the solution 8.9 mg of lithium aluminum hydride was added under cooling with ice. After 30 minutes' stirring, the residual lithium aluminum hydride was quenched with ice pieces, and the reaction liquid was extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and with saturated brine by the order stated, and dried over anhydrous sodium sulfate. Distilling the solvent off from the product, 38 mg of the title compound was obtained.
Workup
- temperatureunder cooling with ice
- customthe residual lithium aluminum hydride was quenched with ice pieces
- customthe reaction liquid
- extractionwas extracted with ethyl acetate
- washThe extract was washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution
- dry with materialdried over anhydrous sodium sulfate
- distillationDistilling the solvent off from the product
Sources & evidence
- ORD record
- ord-616ea7670641498d80bb312f54a4bf53
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040536B2
Reaction notes
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