Pyridine → HCID 131735502, compound

HRID 521712Notes

Reaction equation

[CH2:1]([N:4]([CH2:14][CH:15]=[CH2:16])[CH2:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=O)[CH:2]=[CH2:3].Cl.[NH2:18][OH:19].N1C=CC=CC=1>C(O)C>[CH2:1]([N:4]([CH2:14][CH:15]=[CH2:16])[CH2:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[N:18][OH:19])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 70 °C

Procedure

2-(Diallylamino)-1-(3-pyridyl)ethanone (4.75 g, 21.96 mmol) is dissolved in ethanol (47 mL) under a nitrogen atmosphere. Hydroxylamine hydrochloride (3.55 g, 50.51 mmol) and pyridine (2.5 mL, 30.75 mmol) are then added. The resulting solution is heated at 70° C. under nitrogen for 140 minutes. The reaction is then cooled to room temperature and the solvent is partially evaporated under reduced pressure. The resulting residue is partitioned between 1 M aqueous sodium hydroxide (50 ml) and dichloromethane (250 mL). The phases are separated and the aqueous phase is re-extracted with ethyl acetate (250 mL). The organic layers are combined and the solvents are evaporated. The crude material is purified by silica gel column chromatography using a 0-10% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (3.95 g, 78%) as a mixture of E/Z isomers. ES/MS (m/e): 232 (M+1).

Workup

temperatureThe reaction is then cooled to room temperature
customthe solvent is partially evaporated under reduced pressure
customThe resulting residue is partitioned between 1 M aqueous sodium hydroxide (50 ml) and dichloromethane (250 mL)
customThe phases are separated
extractionthe aqueous phase is re-extracted with ethyl acetate (250 mL)
customthe solvents are evaporated
customThe crude material is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a113bb65d17b4306ab769c950e2248cd
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328124B2

Reaction notes

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