2-(3-formylphenoxy)-N,N-dimethylacetamide → 4-hydroxy-3-[3-[3-[(dimethylaminocarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone

HRID 1669368Notes

Reaction equation

HRID 1669368 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O)=[O:4].[C:16]([C:19]1[C:20](=[O:28])[N:21]([CH3:27])[C:22]([CH3:26])=[CH:23][C:24]=1[OH:25])(=[O:18])[CH3:17]>>[OH:25][C:24]1[CH:23]=[C:22]([CH3:26])[N:21]([CH3:27])[C:20](=[O:28])[C:19]=1[C:16](=[O:18])[CH:17]=[CH:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:5][C:3]([N:2]([CH3:15])[CH3:1])=[O:4])[CH:8]=1

Participants

3

Reactant 2

HCID 144744582-(3-formylphenoxy)-N,N-dimethylacetamideHCID 546917032(1H)-Pyridone, 3-acetyl-4-hydroxy-1,6-dimethyl-

Product 1

HCID 1363442464-hydroxy-3-[3-[3-[(dimethylaminocarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinoneYield 15.7%

Procedure

According to the same manner as that of Example a-1 except that 4.29 g of 3-[(dimethylaminocarbonyl)methoxy]benzaldehyde was used in place of 3-[(methoxycarbonyl)methoxy]benzaldehyde, and 3.40 g of 3-acetyl-4-hydroxy-1,6-dimethyl-2(1H)-pyridinone was used in place of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone, 1.09 g of 4-hydroxy-3-[3-[3-[(dimethylaminocarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (38a)] was obtained as a yellow crystal.

Sources & evidence

ORD record
ord-e7b2ad521d594132ba76b315abb3bbff
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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