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

HRID 1167560Notes

Reaction equation

HRID 1167560 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) δ 8.52 (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-f4a0adcfe66c48ec9fed6bb95e75c21e
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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