Methanol → Methyl 5-chloro-6-hydroxynicotinate

반응식

[Cl:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([OH:11])=[O:10])[CH:3]=1.OS(O)(=O)=O.[CH3:17]O>>[Cl:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([O:11][CH3:17])=[O:10])[CH:3]=1

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 5995415-Chloro-6-hydroxynicotinic acid

생성물 1

HCID 2764225Methyl 5-chloro-6-hydroxynicotinate

실험 절차

A mixture of commercially available 5-chloro-6-oxo-1,6-dihydropyridine-3-carboxylic acid (4.000 g; 23.04 mmol) and concentrated H2SO4 (0.3 ml) in anh. MeOH (52 ml) was refluxed, under nitrogen, for 19 h. MeOH was removed under reduced pressure, and the residue was basified by addition of a solution of 10% aq. NaHCO3. The mixture was then extracted with DCM (5×), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording methyl 5-chloro-6-oxo-1,6-dihydropyridine-3-carboxylate as a pale yellow solid. LC-MS (conditions D): tR=0.61 min.; [M+H]+: 187.93 g/mol.

후처리

temperaturewas refluxed, under nitrogen, for 19 h
customMeOH was removed under reduced pressure
additionthe residue was basified by addition of a solution of 10% aq. NaHCO3
extractionThe mixture was then extracted with DCM (5×)
dry with materialthe mixed organic layers were dried over anh. MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록: ord-0d39eac5cb6c452cadd096f1638b028a
출처 데이터셋: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09242970B2

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