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

HRID 915567Notes

Reaction equation

HRID 915567 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-amine2×

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 (Intermediate F, 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-a4bc11d762e74712857859c543eae138
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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