3-[(2-Methoxyethoxy)carbonylamino]benzaldehyde → 4-hydroxy-3-[3-[3-[(2-methoxyethoxy)carbonylamino]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone

HRID 1669371Notes

Reaction equation

HRID 1669371 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)=[O:7].[C:17]([C:20]1[C:21](=[O:29])[N:22]([CH3:28])[C:23]([CH3:27])=[CH:24][C:25]=1[OH:26])(=[O:19])[CH3:18]>C(O)C>[OH:26][C:25]1[CH:24]=[C:23]([CH3:27])[N:22]([CH3:28])[C:21](=[O:29])[C:20]=1[C:17](=[O:19])[CH:18]=[CH:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([NH:8][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7])[CH:10]=1

Participants

4

Reactant 2

HCID 231318063-[(2-Methoxyethoxy)carbonylamino]benzaldehydeHCID 546917032(1H)-Pyridone, 3-acetyl-4-hydroxy-1,6-dimethyl-

Product 1

HCID 1363442484-hydroxy-3-[3-[3-[(2-methoxyethoxy)carbonylamino]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinoneYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the same manner as that of Example a-1 except that 1.00 g of 3-[(2-methoxyethoxy)carbonylamino]benzaldehyde was used in place of 3-[(methoxycarbonyl)methoxy]benzaldehyde, 0.742 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, and 20 ml of ethanol was used in place of pyridine, 0.96 g of 4-hydroxy-3-[3-[3-[(2-methoxyethoxy)carbonylamino]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (42a)] was obtained as a yellow crystal.

Sources & evidence

ORD record
ord-46fa6e5c6e8948a3b372101c7cbf1405
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

Loading…