Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-1-(4-fluorophenyl)-2-(pyridin-4-yl)prop-2-en-1-one

HRID 54932Notes

Reaction equation

HRID 54932 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>>[CH3:19][N:20]([CH3:22])[CH:21]=[C:9]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:16]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one

Product 1

HCID 545188383-(Dimethylamino)-1-(4-fluorophenyl)-2-(pyridin-4-yl)prop-2-en-1-one

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-fluorophenyl)-2-(pyridin-4-yl)ethan-1-one (5.12 g) and N,N-dimethylformamide dimethyl acetal (16 ml) was stirred at 100° C. for 3 hours under nitrogen. The cooled mixture was concentrated in vacuo. The residue was crystallized from isopropyl ether to yield 3-dimethylamino-1-(4-fluorophenyl)-2-(pyridin-4-yl)-2-propen-1-one (6.15 g).

Workup

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-3207c2d7b59c4a0389289599f8d1f9a9
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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