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

HRID 1795419Notes

Reaction equation

HRID 1795419 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-6a73e4850a334ac6b0c1638fad01aa19
Source dataset
uspto-grants-2006_04
Patent number
US07026476B2

Reaction notes

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