Water → 4-Bromo-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

HRID 2109931Notes

Reaction equation

HRID 2109931 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[N:3]=1.[Br:15]Br.O.[OH-].[K+]>C(O)(=O)C>[Br:15][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[C:5]=1[NH2:7]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24408BromineHCID 7756883-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 47391564-Bromo-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (7.78 g, 41.7 mmol) in acetic acid (90 mL) was added a solution of bromine (6.64 g, 41.6 mmol) in acetic acid (10 mL). The reaction mixture was stirred for 30 min. Water was added to the reaction mixture, and the mixture was basified using a cold KOH solution (1 N). The white solid, 4-bromo-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine, was collected and used in the next step without purification.

Workup

  1. customThe white solid, 4-bromo-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine, was collected
  2. customused in the next step without purification

Sources & evidence

ORD record
ord-1b6ab32c63c6453aa3b7354cfb20f30c
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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