Hydrochloric Acid → 3-tert-Butyl-1-(3-iodo-4-methylphenyl)-1H-pyrazol-5-amine

HRID 431046Notes

Reaction equation

HRID 431046 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][NH2:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16].Cl.[OH-].[Na+]>CCO>[C:12]([C:13]1[CH:14]=[C:15]([NH2:16])[N:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([I:1])[CH:3]=2)[N:10]=1)([CH3:19])([CH3:18])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 22217750HCID 22217750, compound

Product 1

HCID 222178503-tert-Butyl-1-(3-iodo-4-methylphenyl)-1H-pyrazol-5-amineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the above phenylhydrazine (5.08 g, 22 mmol) and 4,4-dimethyl-3-oxopentanenitrile (3.06 g, 1.1 equiv.) in EtOH (100 mL) containing conc. HCl (3 mL) was refluxed for 17 h, then cooled to room temperature. The pH was adjusted to 14 with 40% aqueous sodium hydroxide solution. The aqueous mixture was extracted with EtOAc, (3×50 mL), dried (MgSO4), and concentrated to give 5-tert-butyl-2-(3-iodo-4-methyl-phenyl)-2H-pyrazol-3-ylamine (6.3 g, 86%). This material was used directly without further purification.

Workup

  1. temperaturewas refluxed for 17 h
  2. extractionThe aqueous mixture was extracted with EtOAc, (3×50 mL),
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be33f74733be4c1599d2e32b95b99692
Source dataset
uspto-grants-2003_12
Patent number
US06656933B2

Reaction notes

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