Methanol → 1-(2-Isobutyl-6-methyl-pyridin-4-yl)-ethanone oxime

HRID 1908862Notes

Reaction equation

Cl.[NH2:2][OH:3].[CH2:4]([C:8]1[CH:13]=[C:12]([C:14](=O)[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH:5]([CH3:7])[CH3:6].CO>O.[OH-].[Na+]>[CH2:4]([C:8]1[CH:13]=[C:12]([C:14](=[N:2][OH:3])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH:5]([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of hydroxylamine hydrochloride (120 mg, 1.732 mmol) in water (0.5 mL) and 1 N aq. NaOH (1.2 mL) is added to 1-(2-isobutyl-6-methyl-pyridin-4-yl)-ethanone (276 mg, 1.44 mmol). The solution is stirred at 80° C. for 2 h and MeOH is added to maintain homogeneity of the mixture. The mixture is cooled to rt and the precipitate that forms is collected, washed with water and dried in vacuo to give 1-(2-isobutyl-6-methyl-pyridin-4-yl)-ethanone oxime (258 mg) as a white solid; 1H NMR (D6-DMSO): δ 0.88 (d, J=6.5 Hz, 6H), 1.98-2.10 (m, 1H), 2.13 (s, 3H), 2.45 (s, 3H), 2.56 (d, J=7.0 Hz, 2H), 7.22 (s, 1H), 7.27 (s, 1H), 11.54 (s, 1H).

Workup

temperatureto maintain homogeneity of the mixture
temperatureThe mixture is cooled to rt
customthe precipitate that forms is collected
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-ddd465f31fc64d3d8c226bb32c806c2a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598208B2

Reaction notes

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