Methanol → Methyl 5-chloro-6-hydroxynicotinate
反応式
[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]=1参加物
4
実験手順
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.
後処理
- 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
出典と根拠
- ORDレコード
- ord-0d39eac5cb6c452cadd096f1638b028a
- 出典データセット
- uspto-grants-2016_01
- 特許番号
- US09242970B2
反応ノート
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