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

HRID 1744861Notes

Reaction equation

HRID 1744861 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-b2bcbb2ae7414827b3245111a2b642de
Source dataset
uspto-grants-2006_03
Patent number
US07019006B2

Reaction notes

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