3-(2-Morpholin-4-ylethoxy)benzaldehyde → 4-hydroxy-3-[3-[3-(2-morpholinoethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone

HRID 38308Notes

Reaction equation

HRID 38308 reaction equation
[C:1]([C:4]1[C:5](=[O:12])[NH:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH:25]=O)[CH2:15][CH2:14]1>>[OH:10][C:9]1[CH:8]=[C:7]([CH3:11])[NH:6][C:5](=[O:12])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:25][C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][CH2:20][CH2:19][N:16]2[CH2:17][CH2:18][O:13][CH2:14][CH2:15]2)[CH:23]=1

Participants

3

Reactant 2

HCID 71646203-(2-Morpholin-4-ylethoxy)benzaldehydeHCID 546761542(1H)-Pyridinone, 3-acetyl-4-hydroxy-6-methyl-

Product 1

HCID 1363673464-hydroxy-3-[3-[3-(2-morpholinoethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinoneYield 10.8%

Procedure

According to the same manner as that of Example 16 except that 1.09 g of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone was used in place of 3-acetyl-4-hydroxy-1,6-dimethyl-2(1H)-pyridinone, and 1.68 g of 3-(2-morpholinoethoxy)benzaldehyde was used in place of 3-(methoxycarbonyl)benzaldehyde, 0.27 g of 4-hydroxy-3-[3-[3-(2-morpholinoethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (3a-39)] was obtained as a yellow crystal.

Sources & evidence

ORD record
ord-2cdc646a516c45d1ae54d2ae7e4397e3
Source dataset
uspto-grants-2013_09
Patent number
US08524729B2

Reaction notes

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