Dimethylformamide dimethyl acetal → 3-Dimethylamino-1-(4-chlorophenyl)-2-(pyridin-4-yl)-2-propen-1-one

HRID 1060958Notes

Reaction equation

HRID 1060958 reaction equation
[Cl: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]([Cl:1])=[CH:3][CH:4]=1)=[O:16]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 103990241-(4-Chloro-phenyl)-2-pyridin-4-YL-ethanone

Product 1

HCID 540776133-Dimethylamino-1-(4-chlorophenyl)-2-(pyridin-4-yl)-2-propen-1-oneYield 93%

Procedure

A solution of 4-chlorophenyl-2-(pyridin-4-yl)ethan-1-one (20.0 g, 86.4 mmol) and N,N-dimethylformamide dimethylacetal (57.6 mL, 0.43 mole) was heated at 100° C. for 3½ hours. The reaction mixture was concentrated in vacuo, and the residue crystallized from methyl butyl ether to give 3-dimethylamino-1-(4-chlorophenyl)-2-(pyridin-4-yl)-2-propen-1-one (22.80 g, 93%). 1H NMR (CDCl3/300 MHz) δ8.52 (d, 2H), 7.38 (d, 2H), 7.29 (d, 2H), 7.08 (d, 2H), 2.83 (s, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue crystallized from methyl butyl ether

Sources & evidence

ORD record
ord-49d1a869b9d249f7beeddf10ad57e839
Source dataset
uspto-grants-2003_02
Patent number
US06525059B1

Reaction notes

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