Diethyl Ether → 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

HRID 736292Notes

Reaction equation

HRID 736292 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].C(OCC)C>CCCCCC>[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

5

Reactant 3

HCID 3283Diethyl EtherHCID 95893-AcetylpyridineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneYield 358.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Acetylpyridine (100 g, 0.19 mol) was added to dimethylformamide dimethylacetal (156.5 g, 1.27 mol), and the mixture was reacted under reflux for 23 hours. After the reaction mixture was cooled to 0° C., a mixture of diethyl ether and hexane (3:2, v/v) (500 ml) was added and the whole mixture was stirred for 4 hours. The resulting solid was filtered and washed with a mixture of diethyl ether and hexane (500 ml, 3/2, v/v) to give 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (120 g).

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 23 hours
  3. additionv/v) (500 ml) was added
  4. filtrationThe resulting solid was filtered
  5. washwashed with a mixture of diethyl ether and hexane (500 ml, 3/2

Sources & evidence

ORD record
ord-3ccec616d5c64929ade149537b372c40
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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