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

HRID 1038470Notes

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

Litium 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, 101 mg, 0.323 mmol) was added dropwise thereto at 0° C., and stirred for 1 hour at the same temperature. Ethyl acetate (10 mL), water (10 mL), and 1N aqueous hydrochloride solution (2 mL) were added thereto 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

customsuccessively and the 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-55538f0f00824c7396d5e1204269979e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551991B2

Reaction notes

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