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

HRID 1669381Notes

Reaction equation

HRID 1669381 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)#[N:2].[C:13]([C:16]1[C:17](=[O:25])[N:18]([CH3:24])[C:19]([CH3:23])=[CH:20][C:21]=1[OH:22])(=[O:15])[CH3:14]>C(O)C>[OH:22][C:21]1[CH:20]=[C:19]([CH3:23])[N:18]([CH3:24])[C:17](=[O:25])[C:16]=1[C:13](=[O:15])[CH:14]=[CH:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([CH2:4][CH2:3][C:1]#[N:2])[CH:6]=1

Participants

4

Reactant 2

HCID 114992593-(2-Cyanoethyl)benzaldehydeHCID 546917032(1H)-Pyridone, 3-acetyl-4-hydroxy-1,6-dimethyl-

Product 1

HCID 1363442634-hydroxy-3-[3-[3-(2-cyanoethyl)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinoneYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the same manner as that of Example a-1 except that 0.74 g of 3-(2-cyanoethyl)benzaldehyde was used in place of 3-[(methoxycarbonyl)methoxy]benzaldehyde, 0.93 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 8 ml of ethanol was used in place of pyridine, 0.70 g of 4-hydroxy-3-[3-[3-(2-cyanoethyl)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (106a)] was obtained as a yellow crystal.

Sources & evidence

ORD record
ord-867e9bd47b7d401abb580c5eb84465e6
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

Loading…