Acetonitrile → Methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 2370817ノート

反応式

HRID 2370817 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N+:3]=1[O-:12].CC#N.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:19].C([O-])(O)=O.[Na+]>CO>[OH:12][N:3]1[C:2](=[O:19])[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4]1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 21885872methyl 6-chloronicotinate N-oxide

生成物 1

HCID 21885934Methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
23 °C

実験手順

To a 250 mL round bottom flask containing 2-chloro-5-(methoxycarbonyl)pyridine 1-oxide (2.45 g, 13.06 mmol) was added MeCN (10 mL). The resulting mixture was stirred at 23° C. for 5 min. At this time, trifluoroacetic anhydride (20 mL) was added and the reaction was stirred 1 h. Solid NaHCO3 (25 g) was added to the flask followed by MeOH (100 mL). The solid was filtered away and the filtrate was concentrated and subjected to silica gel chromatography (80 g ISCO column, 0-5% MeOH in CHCl3) to give methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate as a yellow solid.

後処理

  1. stirringthe reaction was stirred 1 h
  2. filtrationThe solid was filtered away
  3. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-12c59c2cd92e48579a3884bee115853e
出典データセット
uspto-grants-2014_04
特許番号
US08710043B2

反応ノート

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