Ethyl 2-oxocyclohexanecarboxylate → 2-(4-Chloro-2-fluoro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahydro-3H-indazol-3-one

HRID 651900Notes

Reaction equation

HRID 651900 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[NH:10][NH2:11].C([O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=O)=O)C>C(O)(=O)C>[Cl:8][C:6]1[C:5]([OH:9])=[CH:4][C:3]([N:10]2[C:15](=[O:14])[CH:17]3[C:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)=[N:11]2)=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 1850812-Chloro-4-fluoro-5-hydrazinylphenol

Product 1

HCID 137530592-(4-Chloro-2-fluoro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahydro-3H-indazol-3-oneYield 85.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-fluoro-4-chloro-5-hydroxyphenylhydrazine (8 g) and 2-ethoxycarbonylcyclohexanone (8 g) in acetic acid (30 ml) was heated under reflux for 4 hours. After cooling, the precipitated crystals were collected by filtration and washed with ether to give 11 g of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahydroindazol-3-one. m.p., 273°-275° C. (decomp.).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with ether

Sources & evidence

ORD record
ord-e57b8d08df194984bffdd0753a4a1853
Source dataset
uspto-grants-1987_06
Patent number
US04670043

Reaction notes

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