5-(Benzyloxy)-1-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid → 3-(benzyloxy)-1-methylpyridin-4(1H)-one

HRID 1187475Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10](=[O:19])[CH:11]=[C:12](C(O)=O)[N:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[CH:11]=[CH:12][N:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 135 °C

Procedure

A suspension of 5-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (18.2 g, 70.2 mmol) in 100 mL of DMF was stirred at oil bath temperature (130-140° C.) for 1.5 h. The reaction mixture was concentrated in vacuo, and the residual oil was diluted with dichloromethane (10 mL) and ethyl acetate (80 mL). The precipitated solid was collected by suction filtration to give 3-benzyloxy-1-methyl-1H-pyridin-4-one as a yellow powder (14.2 g, 94% yield). MS-ESI (m/z): 215.7 [M+1]+, 91.2.

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionthe residual oil was diluted with dichloromethane (10 mL) and ethyl acetate (80 mL)
filtrationThe precipitated solid was collected by suction filtration

Sources & evidence

ORD record: ord-12816820571a4aea95da9907b5340223
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673943B2

Reaction notes

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