Hydrochloric Acid → 2-(2,3-Dimethoxyphenyl)-1-(4-pyridinyl)ethanone

HRID 612494Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:11]=[C:12](NC=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.Cl.[OH-:23].[Na+].O>CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of N-[2-(2,3-dimethoxyphenyl)-1-(4-pyridinyl)vinyl]formamide (45.2 g, 0.16 mol) in methanol (400 ml), cooled to 0° C., was added, dropwise, concentrated HCl (120 ml). After complete addition, the temperature was raised to between 35-40° C. for 2 h. The reaction was allowed to stand at ambient temperature for 1 h, and after cooling it in an ice bath, 50% aqueous NaOH was added dropwise until the mixture was basic. Water was added and the resulting white precipitate was collected to yield the desired ketone which was removed and recrystallized twice from isopropanol to afford the titled compound as a white solid, mp 99-101° C.

Workup

additionwas added
additionAfter complete addition
temperaturethe temperature was raised to between 35-40° C. for 2 h
temperatureafter cooling it in an ice bath
customthe resulting white precipitate was collected

Sources & evidence

ORD record: ord-ed94faed73d04371a3726218742dacbe
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06004982

Reaction notes

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