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

HRID 2370817Notes

Reaction equation

HRID 2370817 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-12c59c2cd92e48579a3884bee115853e
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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