2-Pyridone → HCID 53914177, compound

HRID 1981510Notes

Reaction equation

HRID 1981510 reaction equation
O=C1NC=C([C:11]2[CH:16]=[N:15][CH:14]=[CH:13][N:12]=2)C=C1C(O)=O.[NH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]1=[O:23]>N1C2C(=CC=CC=2)C=CC=1>[N:12]1[CH:11]=[CH:16][N:15]([C:21]2[CH:20]=[CH:19][C:18](=[O:23])[NH:17][CH:22]=2)[CH2:14][CH:13]=1

Participants

4

Reactant 2

HCID 88712-PyridoneHCID 132766762-Oxo-5-(pyrazin-2-yl)-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 53914177HCID 53914177, compound

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

1,2-Dihydro-2-oxo-5-(2-pyrazinyl)nicotinic acid (72.5 g) is added as a fine powder to 800 ml of stirred quinoline heated to just below boiling. The reaction mixture is refluxed for 24 hours, allowed to cool to RT and then placed in an ice bath, and the solid crystallized out. The solid is filtered, washed with ether, dried and recrystallized from isopropanol (first treating with charcoal and filtering while hot) yielding the desired decarboxylated pyridone.

Workup

  1. temperatureheated to just
  2. temperatureThe reaction mixture is refluxed for 24 hours
  3. customplaced in an ice bath
  4. customthe solid crystallized out
  5. filtrationThe solid is filtered
  6. washwashed with ether
  7. customdried
  8. customrecrystallized from isopropanol (first treating with charcoal and filtering while hot)
  9. customyielding the

Sources & evidence

ORD record
ord-f7796daeb3f74a2490109f1adfba8d37
Source dataset
uspto-grants-1986_06
Patent number
US04593028

Reaction notes

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