Dimethylformamide → 5-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone

HRID 638196Notes

Reaction equation

HRID 638196 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[NH2:12])=[CH:5][CH:4]=1.CN(C)C=O.[C:20](OC)(=[O:23])[C:21]#[CH:22]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:10]2[CH:22]=[CH:21][C:20](=[O:23])[NH:12][C:11]=2[CH3:13])=[O:14])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13536Methyl propiolateHCID 15171633-Amino-1-(4-methoxyphenyl)but-2-en-1-one

Product 1

HCID 217799405-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution containing 93 g of 3-(4-methoxyphenyl)-1-methyl-3-oxo-1-propenamine and 200 ml of dimethylformamide was added 46 ml of methyl propiolate over a 30 minute period and the reaction mixture was stirred at ambient temperature for 3 hours and then gently refluxed for 24 hours. The reaction mixture was allowed to cool, treated with 200 ml of isopropyl alcohol and the solid filtered. The solid was washed with isopropyl alcohol and dried at 90°-95° C. to yield, as white shiny crystals, 75.8 g of 5-(4-methoxybenzoyl)-6-methyl-2(1H)-pyridinone, m.p. 228°-230° C.

Workup

  1. temperaturegently refluxed for 24 hours
  2. temperatureto cool
  3. filtrationthe solid filtered
  4. washThe solid was washed with isopropyl alcohol
  5. customdried at 90°-95° C.

Sources & evidence

ORD record
ord-9f008ceff6224592b2d6e489be7d5cfd
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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