Acetic Anhydride → HCID 54547794, compound

HRID 255651Notes

Reaction equation

HRID 255651 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH3:17])=[CH:15][C:14](=[O:18])[C:10]([C:11]([OH:13])=[O:12])=[CH:9]2)=[CH:4][CH:3]=1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.C(OC(=O)C)(=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]=[CH:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:15][C:14](=[O:18])[C:10]([C:11]([OH:13])=[O:12])=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 133894-PyridinecarboxaldehydeHCID 14027755HCID 14027755, compound

Product 1

HCID 54547794HCID 54547794, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.7 g of 1-(4-fluorophenyl)-6-methyl-4-oxo-1,4-dihydronicotinic acid was added 0.33 g of isonicotinaldehyde and 0.61 g of acetic anhydride, and they were refluxed for 5 hours. After completion of the reaction, 30 ml of water was added to the reaction mixture, and the mixture was successively extracted with three 30-ml portions of chloroform. The chloroform layer was separated, washed with 20 ml of a saturated aqueous solution of sodium chloride, and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 0.42 g of 1-(4-fluorophenyl)-6-[2-(pyridin-4-yl)ethenyl]-4-oxo-1,4-dihydronicotinic acid having a melting point of 205°-215° C.

Workup

  1. temperaturewere refluxed for 5 hours
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was successively extracted with three 30-ml portions of chloroform
  4. customThe chloroform layer was separated
  5. washwashed with 20 ml of a saturated aqueous solution of sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-91e4ca6d55aa415fa706c6b223c9cbf9
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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