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

HRID 2370817노트

반응식

HRID 2370817 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
23 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-12c59c2cd92e48579a3884bee115853e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710043B2

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