Water → 7-(5-Chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871974Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:25]=[C:24]2[C:11]([O:12][C:13](=[O:30])[C:14]3[C:23]2=[CH:22][CH:21]=[C:20]2[C:15]=3[N:16]([CH3:29])[C:17](=[O:28])[C:18]([CH3:27])([CH3:26])[NH:19]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.O>O1CCCC1.[Cl-].[Na+].O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:12])=[C:24]([C:23]2[C:14]([CH2:13][OH:30])=[C:15]3[C:20]([NH:19][C:18]([CH3:26])([CH3:27])[C:17](=[O:28])[N:16]3[CH3:29])=[CH:21][CH:22]=2)[CH:25]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Lithium aluminium hydride (442 mg, 11.7 mmol) was suspended in anhydrous tetrahydrofuran (10 mL) under nitrogen atmosphere. An anhydrous tetrahydrofuran solution (40 mL) of 9-chloro-2,2,4-trimethyl-1,4-dihydro-2H-6-oxa-1,4-diazachrysen-3,5-dione (Reference Compound No. 11-1, 1:99 g, 5.81 mmol) was added dropwise thereto at −10° C. and stirred for 10 minutes at the same temperature. After ethyl acetate (1 mL) and water (1 mL) were added thereto successively, ethyl acetate (300 mL) and saturated brine (300 mL) were added and partitioned. The organic layer was washed with saturated brine (150 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 (1.38 g) as a pale yellow solid. (Yield 69%)

Workup

custompartitioned
washThe organic layer was washed with saturated brine (150 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-b3d06372cfef4a94acaf71fc7e9678df
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975256B2

Reaction notes

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