2-Oxocyclohexanecarboxamide → 3H-Indazol-3-one

HRID 1390669Notes

Reaction equation

HRID 1390669 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[C:5](F)[CH:4]=1.C1CC(C(N)=O)[C:15](=[O:16])CC1>>[N:9]1[C:6]2[C:5](=[CH:4][CH:3]=[CH:8][CH:7]=2)[C:15](=[O:16])[N:10]=1

Participants

3

Reactant 2

HCID 5879892-OxocyclohexanecarboxamideHCID 2782933(4-Chloro-2-fluorophenyl)hydrazine hydrochloride

Product 1

HCID 133404823H-Indazol-3-one

Procedure

The pH of the 4-chloro-2-fluorophenylhydrazine hydrochloride slurry was adjusted to 3.8-4.0 and the temperature was raised to 90°-95°. To this mixture was added an aqueous solution (preheated to 90°-95°) of 1118 parts of cyclohexanone-2-carboxamide prepared as previously described. The resulting mixture was heated for 1-2 hr at 90°-95° during which time the product precipitated from solution. The product was isolated by filtration, washed by digestion with toluene and air-dried to give 1771 parts of an indazolone, an off-white solid mp 179-182 which was 2-(4-chloro-2-fluorophenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one.

Workup

  1. temperaturethe temperature was raised to 90°-95°
  2. customprepared
  3. temperatureThe resulting mixture was heated for 1-2 hr at 90°-95° during which time the product
  4. customprecipitated from solution
  5. customThe product was isolated by filtration
  6. washwashed by digestion with toluene
  7. customair-dried

Sources & evidence

ORD record
ord-63bfdf5c47e143868bf4baba4812ac63
Source dataset
uspto-grants-1979_02
Patent number
US04139710

Reaction notes

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