1,2-Dichloroethane → 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4,5-dimethoxy-phenyl)-amide

HRID 1012143Notes

Reaction equation

HRID 1012143 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[N+:22]([C:25]1[C:26]([C:30]([OH:32])=O)=[N:27][NH:28][CH:29]=1)([O-:24])=[O:23].Cl.Cl.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([NH2:46])[C:40]([NH2:45])=[CH:41][C:42]=1[O:43][CH3:44]>CN(C=O)C>[NH2:45][C:40]1[CH:41]=[C:42]([O:43][CH3:44])[C:37]([O:36][CH3:35])=[CH:38][C:39]=1[NH:46][C:30]([C:26]1[C:25]([N+:22]([O-:24])=[O:23])=[CH:29][NH:28][N:27]=1)=[O:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 130002194,5-Dimethoxybenzene-1,2-diamine--hydrogen chloride (1/2)HCID 178524956HCID 178524956, compound

Product 1

HCID 1784932234-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4,5-dimethoxy-phenyl)-amideYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EDC (4.81 g, 25 mmol), HOBt (3.40 g, 25 mmol) and triethylamine (4.67 g, 46 mmol) in DMF (100 ml) was added 4-nitro-1H-pyrazole-3-carboxylic acid (3.63 g, 23.09 mmol) and 4,5-dimethoxy-benzene-1,2-diamine, dihydrochloride (5.06 g, 20.99 mmol) and the mixture stirred at room temperature overnight. The solvent was removed in vacuo and the resulting solid partitioned between ethyl acetate (50 ml) and sodium bicarbonate (50 ml). A precipitate was formed and removed by filtration. This was washed with water followed by diethyl ether and then azeotroped with methanol and toluene to yield 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4,5-dimethoxy-phenyl)-amide (2.35 g, 36%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting solid partitioned between ethyl acetate (50 ml) and sodium bicarbonate (50 ml)
  3. customA precipitate was formed
  4. customremoved by filtration
  5. washThis was washed with water
  6. customazeotroped with methanol and toluene

Sources & evidence

ORD record
ord-2ddc32bcf1f949ac91052dc6ee73d00f
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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