Cyclohexanone → 4-cyclohex-1-enyl-5-methyl-2-phenyl-2H-pyrazol-3-ylamine

HRID 1034951Notes

Reaction equation

HRID 1034951 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)(=O)C>[C:14]1([C:3]2[C:4]([CH3:13])=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:2]=2[NH2:1])[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 708015-Amino-3-methyl-1-phenylpyrazole

Product 1

HCID 694762524-cyclohex-1-enyl-5-methyl-2-phenyl-2H-pyrazol-3-ylamineYield 74.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-amino-3-methyl-1-phenylpyrazole (8.66 g, 50 mmol) in acetic acid (70 mL) was treated with cyclohexanone (10.6 mL, 100 mmol) at ambient temperature for 40 hours. The volatiles were removed and the residue diluted with water and 10% sodium hydroxide added until the pH=12. The mixture was stirred with 10 mL of hexane for 30 minutes and the solid collected by filtration, washed with water and hexane and dried to give 9.43 g (74%) of the title compound. MS (DCI): m/z 254 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. additionthe residue diluted with water and 10% sodium hydroxide
  3. additionadded until the pH=12
  4. filtrationthe solid collected by filtration
  5. washwashed with water and hexane
  6. customdried

Sources & evidence

ORD record
ord-9062883a5b4e4ff0b89f3a0092b22c31
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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