Acetic Anhydride → Methyl 4-(2-oxo-1,2-dihydropyridin-3-yl)benzoate

HRID 910614Notes

Reaction equation

[O-][N+:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[CH:3]=1.C(OC(=O)C)(=[O:20])C>>[O:20]=[C:3]1[C:4]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:6]=[CH:7][NH:2]1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 18182583Methyl 4-(1-oxidopyridin-3-yl)benzoate

Product 1

HCID 53217923Methyl 4-(2-oxo-1,2-dihydropyridin-3-yl)benzoate

Conditions

Temperature: 130 °C

Procedure

Acetic anhydride (20 mL) was added to methyl 4-(1-oxidopyridin-3-yl)benzoate (704 mg), followed by stirring at 130° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, followed by two times azeotropy with toluene. The resulting residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 10%) to obtain methyl 4-(2-oxo-1,2-dihydropyridin-3-yl)benzoate (651 mg) as a pale brown solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe resulting residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 10%)

Sources & evidence

ORD record: ord-36122dd6d85a4a6abe5e8d8eece567fb
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022208B2

Reaction notes

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