Acetic Acid → HCID 178526878, compound

HRID 1978165Notes

Reaction equation

HRID 1978165 reaction equation
C([C:3]1[C:4](=[O:11])[NH:5][CH:6]=[CH:7][C:8]=1[O:9]C)#N.C(O)(=O)C.[N+:16]([O-])([OH:18])=[O:17]>O>[OH:11][C:4]1[C:3]([N+:16]([O-:18])=[O:17])=[C:8]([OH:9])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

Product 1

HCID 178526878HCID 178526878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
177.5 °C

Procedure

86% phosporic acid (90 mL, 151.3 g) and 3-cyano-4-methoxy-2(1H)-pyridinone (Compound X) (30.0 g, 0.20 mole) are combined under argon in a 500 mL flask equipped with a mechanical stirrer, reflux condensor. The mixture is heated in an oil bath at 175-180° C. for 23 hours. The reaction mixture is cooled to 71° C. and glacial acetic acid (90 mL, 94.5 g) added and the mixture heated at 90° C. for about 90 minutes. Fuming nitric acid (density=1.52) (12.6 g, 8.3 ml) is then added carefully over a period of 15 minutes (giving a mild exotherm), and the mixture heated at 90-95° C. for 2 hours. Water (90 mL) is then added to the mixture and heating at 90° C. continued for 1 hour. The mixture is then cooled slowly with stirring to room temperature, filtered through a sintered glass funnel and the residue washed with water to give Compound XII, m.p. 268° C.; NMR (DMSO) δ 7.44 (1H, d); 6.0 (1H, d); 3.5 (2H).

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condensor
  3. temperatureThe reaction mixture is cooled to 71° C.
  4. temperaturethe mixture heated at 90° C. for about 90 minutes
  5. customgiving a mild exotherm), and the mixture
  6. temperatureheated at 90-95° C. for 2 hours
  7. temperatureheating at 90° C.
  8. temperatureThe mixture is then cooled slowly
  9. filtrationfiltered through a sintered glass funnel
  10. washthe residue washed with water

Sources & evidence

ORD record
ord-95347baa89dc4c30a2a36740b3c1714f
Source dataset
uspto-grants-2001_05
Patent number
US06235909B1

Reaction notes

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