Methanol → HCID 178499180, compound

HRID 2064684Notes

Reaction equation

HRID 2064684 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([OH:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:12](Cl)(=O)C(Cl)=O.CO>ClCCl.CN(C)C=O>[CH3:12][O:10][C:9]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=1)=[O:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 178524956HCID 178524956, compound

Product 1

HCID 178499180HCID 178499180, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 4-nitro-3-pyrazolecarboxylic acid (1 g) in dichloromethane under nitrogen at 0° C. was treated with oxalyl chloride (1.11 ml) followed by dimethylformamide (5 drops). The reaction mixture was warmed to room temperature and stirred overnight. Methanol (10 ml) was added and the reaction mixture was stirred overnight. The solvent was removed under reduced pressure and azeotroped with toluene twice to yield 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.3 g) as a pale green solid. LC-MS (Method H): RT=1.94 minutes, 170.23 (M−H)−.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe solvent was removed under reduced pressure
  3. customazeotroped with toluene twice

Sources & evidence

ORD record
ord-f832dcb3479c4c00ab5bee133400fd1a
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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