Acetic Acid → 3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

HRID 2049319Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].CI.[C:21](O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]([CH3:21])[C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one (2.2 g) in dry toluene (40 ml) was added dropwise to a stirred suspension of sodium hydride (0.62 g, 0.015 mole of 50% dispension in oil, pre-washed with dry light petroleum (b.p. 40°-60°). After stirring and heating at 60° for 1 hour the reaction was cooled to 5° C. and methyl iodide (1.9 ml, 2.5 g, 0.02 mole) was added rapidly. After stirring at ambient temperature for 20 hours acetic acid and water were added. The aqueous layer was separated and washed with toluene. Toluene extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated to an oil. Oil was recrystallised from ethylacetate light petroleum (b.p. 60°-80°) affording 1.95 g (83%) of hexahydro-(3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one, in several crops, m.p. 74°-5° C.

Workup

washpre-washed with dry light petroleum (b.p. 40°-60°)
temperatureheating at 60° for 1 hour the reaction
additionwere added
customThe aqueous layer was separated
washwashed with toluene
washToluene extracts were washed with water
dry with materialdried over anhydrous magnesium sulphate
customevaporated to an oil
customOil was recrystallised from ethylacetate light petroleum (b.p. 60°-80°)

Sources & evidence

ORD record: ord-e3ce159866da4bf5b5387d503050b811
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04197241

Reaction notes

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