Water → 4'-Nitro-2-hydroxyacetophenone O-methyloxime

HRID 977068Notes

Reaction equation

Cl.[CH3:2][O:3][NH2:4].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][O:16][Si](C(C)(C)C)(C)C)=[CH:10][CH:9]=1)([O-:7])=[O:6].O1CCOCC1.O>CO>[CH3:2][O:3][N:4]=[C:14]([C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=1)[CH2:15][OH:16]

Participants

Conditions

Temperature: 80 °C

Procedure

69 mg of O-methylhydroxylamine hydrochloride were added to a solution of 0.12 g (0.41 mmol) of 4'-nitro-2-t-butyldimethylsilyloxyacetophenone (obtained above) in a mixture of methanol (1.2 ml), 1,4-dioxane (2.0 ml) and water (2.0 ml). The resulting mixture was stirred for 1.5 hours at 80° C., then poured into water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography, eluted with a stepwise gradient of ethyl acetate (10-40%) in hexane, to give 58 mg (67% yield) of the title compound.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customThe residue was purified by silica gel column chromatography
washeluted with a stepwise gradient of ethyl acetate (10-40%) in hexane

Sources & evidence

ORD record: ord-fe6957ee84a24596bcaa962508debe81
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614470

Reaction notes

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