Acetic Acid → HCID 18964014, compound

HRID 2226917Notes

Reaction equation

HRID 2226917 reaction equation
C(O)(=O)C.Cl.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1.O=[C:17]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18]1>O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:17]3[CH2:18][CH:19]([C:22]([OH:24])=[O:23])[CH2:20][C:21]=3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2277983-Oxocyclopentanecarboxylic acidHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 18964014HCID 18964014, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 250 ml of 80% acetic acid in water were added 4-methoxyphenylhydrazine hydrochloride (21 g, 0.12 mole) and 3-oxocyclopentane carboxylic acid (20 g, 0.15 mole). After stirring at ambient temperature for two hours, the mixture was stirred at 100° C. for three hours. After cooling, the mixture was filtered, and the tan precipitate washed with water, and dried to give 15 g of a solid, mp ~200° C. A sample of this material was recrystallized from ethanol/ether (1:2) to give a tan solid, mp 210° C. (dec.).

Workup

  1. stirringthe mixture was stirred at 100° C. for three hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washthe tan precipitate washed with water
  5. customdried

Sources & evidence

ORD record
ord-d8d4757aa2774bec84e92703db1d2ed8
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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