Acetic Acid → 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole

HRID 651901Notes

Reaction equation

HRID 651901 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][NH2:10])=[C:4]([F:11])[CH:3]=1.[C:12]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=O)(=O)[CH3:13].C(O)(=O)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:12]([CH3:13])=[C:15]3[C:16]([CH2:17][CH2:18][CH2:19][CH2:20]3)=[N:10]2)=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 134002-AcetylcyclohexanoneHCID 1850812-Chloro-4-fluoro-5-hydrazinylphenol

Product 1

HCID 136871962-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazoleYield 88.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Chloro-2-fluoro-5-hydroxyphenylhydrazine (0.5 g), 2-acetylcyclohexanone (0.4 g) and a catalytic amount of acetic acid were admixed with xylene (15 ml), and the resultant mixture was heated under reflux for 5 hours while removing water. After cooling, the mixture was concentrated, and the residue was purified by silica gel column chromatography to obtain 0.7 g of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole. m.p., 188.5°-190° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customwhile removing water
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1cc023d09054c9db329acc067e4e7f1
Source dataset
uspto-grants-1987_06
Patent number
US04670043

Reaction notes

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