Acetic Acid → HCID 23044837, compound

HRID 986598Notes

Reaction equation

HRID 986598 reaction equation
[C:1]1([C:7]2O[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:10][C:11](=[O:18])[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C(O)(=O)C.[CH2:31]([NH2:33])[CH3:32]>O>[CH2:31]([N:33]1[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][C:11](=[O:18])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:32]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 6341EthylamineHCID 14075266HCID 14075266, compound

Product 1

HCID 23044837HCID 23044837, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.5 gms of 2,6-diphenyl-3-ethoxycarbonyl-pyr-4-one, 33 mls of methanol, 5 mls of water and 2 mls of glacial acetic acid were mixed. 7.6 mls of 70% aqueous ethylamine was then added slowly and the resulting mixture was allowed to stand at room temperature for 24 hours. The mixture was then diluted with 100 mls of water. The pH was adjusted to 2. Extraction with methylene chloride and evaporation of the solvent provided 3.0 gms of crude ethyl 1-ethyl-2,6-diphenyl-4-oxonicotinate as a brown oil. This material was dissolved in 20 mls of methanol. This solution was then added to 40 mls of 5% aqueous NaOH and heated on a steambath for 5 hours. The reaction mixture was cooled and acidified. Extraction with methylene chloride (3×50 mls) yielded an oily solid after evaporation. Crystallization from methylene chloride/ether yielded 1.6 gms of 1-ethyl-2,6-diphenyl-4-oxonicotinic acid. mp=210°-3° (dec).

Workup

  1. extractionExtraction
  2. customwith methylene chloride and evaporation of the solvent

Sources & evidence

ORD record
ord-4827edfabd494cf496a4c8e0e4aafeb3
Source dataset
uspto-grants-1987_12
Patent number
US04714492

Reaction notes

Loading…