4,5-Dimethyl-1,2-phenylenediamine → HCID 178428586, compound

HRID 2064663Notes

Reaction equation

HRID 2064663 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.C(N(C(C)C)CC)(C)C.[N+:20]([C:23]1[C:24]([C:28](Cl)=[O:29])=[N:25][NH:26][CH:27]=1)([O-:22])=[O:21]>ClCCl>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=1[NH:10][C:28]([C:24]1[C:23]([N+:20]([O-:22])=[O:21])=[CH:27][NH:26][N:25]=1)=[O:29]

Participants

5

Reactant 3

HCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 81531DiisopropylethylamineHCID 178521133HCID 178521133, compound

Product 1

HCID 178428586HCID 178428586, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Method A A stirred solution of 4,5-dimethylphenylenediamine (4.32 g) and diisopropylethylamine (30 ml) in dichloromethane (200 ml) was treated with 4-nitropyrazole-3-carboxylic chloride (5 g) portionwise at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 30 minutes. The solvent was removed in vacuo and the oily residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and concentrated. The residual oil was re-crystallised from ethyl acetate and methanol (10%) to give 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4,5-dimethylphenyl)amide (6.58 g) as an orange solid. LC-MS (METHOD B): RT=2.36 minutes, 276.09 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe oily residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residual oil was re-crystallised from ethyl acetate and methanol (10%)

Sources & evidence

ORD record
ord-c29862aa360e4e8591232b490976eaf8
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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