4-Hydrazinobenzoic acid → 4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid

HRID 1661003

Reaction equation

HRID 1661003 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].[C:12]([CH2:18][C:19]#[N:20])(=O)[C:13]([CH3:16])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[NH2:20][C:19]1[N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[N:2]=[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:18]=1

Participants

4

Reactant 2

HCID 120894-Hydrazinobenzoic acidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 9746884-(5-Amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2.4 g (16 mmol) 4-hydrazino-benzoic acid in 12 mL toluene, 2.0 g of pivaloyl acetonitrile are added at rt. The suspension is heated to and kept under reflux for 12 h. After completion, the resulting reaction mixture is allowed to cool to rt. The precipitated product is isolated by filtration, washed with cold toluene and dried under high vacuum. [M+1]+=260.

Workup

  1. additionare added at rt
  2. temperatureThe suspension is heated to and
  3. temperatureunder reflux for 12 h
  4. customAfter completion, the resulting reaction mixture
  5. customThe precipitated product is isolated by filtration
  6. washwashed with cold toluene
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-cc0f4202c7ad45a6903e387b1dfd118c
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Linked notes

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