tert-Butoxy bis(dimethylamino)methane → 6-[2-(dimethylamino)ethenyl]-5-(4-methoxybenzoyl)-2(1H)-pyridinone

HRID 638204Notes

Reaction equation

HRID 638204 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[O:8])=[CH:5][CH:4]=1.[CH3:19][N:20]([CH:22](N(C)C)OC(C)(C)C)[CH3:21]>O1CCOCC1>[CH3:19][N:20]([CH3:22])[CH:21]=[CH:15][C:14]1[NH:13][C:12](=[O:16])[CH:11]=[CH:10][C:9]=1[C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 217799405-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone

Product 1

HCID 545623996-[2-(dimethylamino)ethenyl]-5-(4-methoxybenzoyl)-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture containing 50 g of 5-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone, 400 ml of p-dioxane and 40 ml of bis(dimethyamino)-t-butoxymethane was refluxed with stirring for 5 and 1/2 hours. The reaction mixture was allowed to cool and the separated crystalline product was collected, washed with ethanol and dried in a vacuum oven at 80°-85° C., to yield 65.8 g of 6-[2-(dimethylamino)ethenyl]-5-(4-methoxybenzoyl)-2(1H)-pyridinone, m.p. 216°-218° C.

Workup

  1. temperaturewas refluxed
  2. temperatureto cool
  3. customthe separated crystalline product was collected
  4. washwashed with ethanol
  5. customdried in a vacuum oven at 80°-85° C.

Sources & evidence

ORD record
ord-ba2b7d520e2d404f80adc59e959bfc89
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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