Dimethylformamide diethylacetal → 3-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-one

HRID 724816Notes

Reaction equation

HRID 724816 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([Cl:10])[CH:5]=1)(=[O:3])[CH3:2].C(O[CH:14](OCC)[N:15]([CH3:17])[CH3:16])C>>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([Cl:10])[CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-one

Procedure

16.2 g (104.2 mmol) of 4-acetyl-2-chloro-pyridine are stirred for 1 hour at 110° with 116 ml of dimethylformamide diethylacetal. After cooling to 0°, filtering and drying at 60° under HV, 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one is obtained; 1 H-NMR (dimethyl sulfoxide): 2.98 (3H,s), 3.2 (3H,s), 5.9 (1H,d), 7.8 (3H,m), 8.5 (1H,d).

Workup

  1. temperatureAfter cooling to 0°
  2. filtrationfiltering
  3. customdrying at 60° under HV

Sources & evidence

ORD record
ord-0912afa843954f5b917e6f3438df3c09
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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