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

HRID 2230380Notes

Reaction equation

HRID 2230380 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-52fed9ebefb74a8188d70b01503f5950
Source dataset
uspto-grants-2002_07
Patent number
US06423713B1

Reaction notes

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