Acetic Acid → 2-Phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one

HRID 1703436Notes

Reaction equation

HRID 1703436 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)([O:3]C)=O.[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.C(O)(=O)C>O>[C:12]1([N:18]2[C:1](=[O:3])[C:5]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[NH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 7516PhenylhydrazineHCID 170489Cyclohexanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 31161752-Phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

32.9 Parts of a mixture containing 60% 2-carboethoxyclohexanone and 40% of 2-carbomethoxycyclohexanone purchased from Aldrich Chemical Company, Milwaukee, Wisconsin 53233, and 21.6 parts of phenylhydrazine purchased from Eastman Organic Chemicals Company, Rochester, N. Y. 14650, were admixed in 200 parts of toluene containing 2.0 parts of acetic acid. The mixture was refluxed for two hours with water removal. The resulting yellow suspension was cooled to 0°. The solid was collected, washed with hexane and dried. The yield was 37.1 parts of white solid with m.p. 178°-181°.

Workup

  1. addition32.9 Parts of a mixture containing 60% 2-carboethoxyclohexanone
  2. temperatureThe resulting yellow suspension was cooled to 0°
  3. customThe solid was collected
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-be914280c2b748fa9054d9dd8b7a7b22
Source dataset
uspto-grants-1978_11
Patent number
US04124373

Reaction notes

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