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

HRID 509378Notes

Reaction equation

HRID 509378 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 awau 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 awau
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bbb27f7b6fcd4ea08910ecbfa13e2ade
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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