Oxalyl chloride → 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4-methoxy-phenyl)-amide

HRID 2064665Notes

Reaction equation

HRID 2064665 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1.[N+:11]([C:14]1[C:15]([C:19](Cl)=[O:20])=[N:16][NH:17][CH:18]=1)([O-:13])=[O:12].[N+](C1C(C(O)=O)=NNC=1)([O-])=O.C(Cl)(=O)C(Cl)=O>ClCCl.CN(C)C=O>[NH2:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][C:19]([C:15]1[C:14]([N+:11]([O-:13])=[O:12])=[CH:18][NH:17][N:16]=1)=[O:20]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 1534044-Methoxy-o-phenylenediamineHCID 178521133HCID 178521133, compoundHCID 178524956HCID 178524956, compound

Product 1

HCID 1784923544-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4-methoxy-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

By proceeding in a manner similar to Reference Example 36(a), Method A, above but using 4-methoxy-1,2-phenylenediamine (880 mg) and 4-nitropyrazole-3-carboxylic chloride [prepared by treating a solution of 4-nitropyrazole-3-carboxylic acid (1 g) in dry dichloromethane (70 ml) under nitrogen with oxalyl chloride (1.11 ml) and dimethylformamide and after stirring overnight evaporating the reaction mixture then azeotroping three times with toluene (10 ml)] there was prepared 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4-methoxy-phenyl)-amide (800 mg). LC-MS (Method J): RT=2.67 minutes, 278.25 (M+H)+, 276.28 (M−H)−.

Workup

  1. customprepared
  2. customevaporating the reaction mixture
  3. customthen azeotroping three times with toluene (10 ml)] there
  4. customwas prepared 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4-methoxy-phenyl)-amide (800 mg)

Sources & evidence

ORD record
ord-76e6b79a25784d3daf4182715875f18d
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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