Hydroxyamine hydrochloride → 1-(1,2-dimethyl-1H-imidazol-5-yl)-N-hydroxy-1-phenylmethanimine

HRID 875216Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[CH:5][N:4]=[C:3]1[CH3:15].Cl.[NH2:17][OH:18]>N1C=CC=CC=1>[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:17][OH:18])=[CH:5][N:4]=[C:3]1[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methanone (8.41 g, 42 mmol) and hydroxylamine hydrochloride (7.30 g, 105 mmol) in pyridine (60 mL) was stirred for 5 h at room temperature, and for 3 h at 50° C. Hydroxylamine hydrochloride (3.00 g, 43 mmol) was added again and the reaction mixture was stirred for 9.5 h at 50° C. After removal of the solvent in vacuo and addition of water (600 mL), the pH of the aqueous solution was adjusted to pH>7 by addition of aq. NaOH (1 M). After extraction with ethyl acetate (4×150 mL), the combined organic layers were washed with water (150 mL), dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded 1-(1,2-dimethyl-1H-imidazol-5-yl)-N-hydroxy-1-phenylmethanimine [2.31 g, yield 24%; HPLC/MS: m/z=216 (M+H); log P(HCOOH)=0.43].

Workup

customAfter removal of the solvent
additionin vacuo and addition of water (600 mL)
additionthe pH of the aqueous solution was adjusted to pH>7 by addition of aq. NaOH (1 M)
extractionAfter extraction with ethyl acetate (4×150 mL)
washthe combined organic layers were washed with water (150 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification on silica gel

Sources & evidence

ORD record: ord-e4dab88705ff45f8aa706330743f1464
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981111B2

Reaction notes

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