3-Acetylpyridine → 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

HRID 2387183Notes

Reaction equation

HRID 2387183 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>>[CH3:12][N:13]([CH3:15])[CH:14]=[CH:2][C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

3

Reactant 2

HCID 95893-AcetylpyridineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

Procedure

Reactant 3 can be obtained by the following procedures. A mixture of 3-acetylpyridine (2.47 mol) and N,N-dimethylformamide dimethylacetal (240 mL) is heated at reflux for 16 h. The solvent is removed in vacuo and hexanes (100 mL) is added to the residue to crystallize a solid. The solid is recrystallized from methylene chloride-hexanes to give 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one. 1H NMR (400 MHz, d-chloroform) δ 9.08 (d, J=2.4 Hz, 1H), 8.66 (m, 1H), 8.20 (m, 1H), 7.87 (m, 1H), 7.37 (m, 1H), 5.68 (d, J=16.4 Hz, 1H), 3.18 (s, 3H), 2.97 (s, 3H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 h
  3. customThe solvent is removed in vacuo and hexanes (100 mL)
  4. additionis added to the residue
  5. customto crystallize a solid
  6. customThe solid is recrystallized from methylene chloride-hexanes

Sources & evidence

ORD record
ord-497e23dd1fbd4788aa13ded72fcc0a92
Source dataset
uspto-grants-2012_09
Patent number
US08268850B2

Reaction notes

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