Hydrochloric Acid → 7-Bromo-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1182761Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[C:17]([C:18](OC)=[O:19])=[C:16]2[C:11]([NH:12][C:13]([CH3:24])([CH3:23])[C:14](=[O:22])[NH:15]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.Cl>O1CCCC1.O>[Br:7][C:8]1[C:17]([CH2:18][OH:19])=[C:16]2[C:11]([NH:12][C:13]([CH3:24])([CH3:23])[C:14](=[O:22])[NH:15]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (38.5 mg, 1.01 mmol) was suspended in anhydrous tetrahydrofuran (0.5 mL) under nitrogen atmosphere. An anhydrous tetrahydrofuran solution (1.5 mL) of 7-bromo-8-methoxycarbonyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 1-(6), 101 mg, 0.323 mmol) was added dropwise thereto at 0° C., and the mixture was stirred for 1 hour at the same temperature. Ethyl acetate (10 mL), water (10 mL), and 1N aqueous HCl solution (2 mL) were added to the reaction mixture successively and the mixture was partitioned. The organic layer was washed with saturated brine (10 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (67.4 mg) as an orange amorphous product. (Yield 74%)

Workup

addition1-(6), 101 mg, 0.323 mmol) was added dropwise
customthe mixture was partitioned
washThe organic layer was washed with saturated brine (10 mL)
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-eebce0b27bea4cfe9b6a0171e10a1075
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664221B2

Reaction notes

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