Acetic Acid → HCID 14075379, compound

HRID 2107931Notes

Reaction equation

HRID 2107931 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]CC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[CH2:29]([NH2:32])[CH2:30][CH3:31].Cl>O.CO>[CH2:29]([N:32]1[C:9]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:10][C:11](=[O:18])[C:12]([C:13]([OH:15])=[O:14])=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7852PropylamineHCID 14075266HCID 14075266, compound

Product 1

HCID 14075379HCID 14075379, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

4.0 gms of 2,6-diphenyl-3-ethoxycarbonyl-pyr-4-one, 50 mls of glacial acetic acid were mixed. 8.1 gms of n-propylamine and 6 mls of water was added slowly at room temperature. After 3 hours an additional 14 mls of water, 12 mls of 6% HCl and enough methanol to bring everything into solution, was added. The next day this acidic reaction misture was poured into water and extracted with methylene chloride (2×100 mls). Evaporation of the organic extracts yield 4.4 gms of crude nicotinate ester which was suspended in 50 mls of 5% aqueous NaOH and heated at 85° for 4 hours. The resulting solution was acidified with HCl and extracted with methylene chloride (2×50 mls). Evaporation of the solvent yielded a solid mass. Recrystallization from ether provided 1.5 gms of 1-propyl-2,6-diphenyl-4-oxonicotinic acid. mp=166°-7°.

Workup

  1. additioneverything into solution, was added
  2. extractionextracted with methylene chloride (2×100 mls)
  3. customEvaporation of the organic extracts yield 4.4 gms of crude nicotinate ester which
  4. temperatureheated at 85° for 4 hours
  5. extractionextracted with methylene chloride (2×50 mls)
  6. customEvaporation of the solvent
  7. customyielded a solid mass
  8. customRecrystallization from ether

Sources & evidence

ORD record
ord-b1d675bea62247b7beeab41692f1a1ed
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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