O-Xylene → 2-(4-chloro-2-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole

HRID 1703444Notes

Reaction equation

HRID 1703444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[C:4]([F:10])[CH:3]=1.[C:11]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O)(=O)[CH3:12].C1(C)C(C)=CC=CC=1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11]([CH3:12])=[C:14]3[C:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)=[N:9]2)=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 134002-AcetylcyclohexanoneHCID 2782934(4-Chloro-2-fluorophenyl)hydrazine

Product 1

HCID 212012922-(4-chloro-2-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 19.7 parts of 4-chloro-2-fluorophenylhydrazine and 14.0 parts of 2-acetylcyclohexanone in 50 parts of xylene and 1 part of glacial acetic acid were refluxed for 24 hours with a Dean Stark trap to collect the water formed. The xylene was distilled from the mixture. The residual oil was dissolved in arm hexane solution. On cooling, 6.2 parts of crude product was obtained. Recrystallization of this product yielded white crystals of 2-(4-chloro-2-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole, melting point 84.5°-87.5° C; ir bands (1570 cm-1, 905 cm-1, 822 cm-1).

Workup

  1. customto collect the water
  2. customformed
  3. distillationThe xylene was distilled from the mixture
  4. dissolutionThe residual oil was dissolved in arm hexane solution
  5. temperatureOn cooling
  6. custom6.2 parts of crude product was obtained
  7. customRecrystallization of this product

Sources & evidence

ORD record
ord-e1c1d5515edd487ab21f4946fcf04def
Source dataset
uspto-grants-1978_11
Patent number
US04124374

Reaction notes

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