Methylamine → N,1-dimethyl-4-nitropyrazole-3-carboxamide

HRID 1045954Notes

Reaction equation

HRID 1045954 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.C1N=C[N:15](C(N2C=NC=C2)=O)[CH:14]=1.CN>C1COCC1>[CH3:14][NH:15][C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 1256475N,1-dimethyl-4-nitropyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 1-methyl-4-nitropyrazole-3-carboxylic acid (2.0 g) in THF (30 ml) was charged carbonyl-1,1′-diimidazole (1.9 g) over 1 hour at room temperature. The reaction was stirred overnight before cooling to 0° C. A solution of methylamine in THF (12 ml of a 2M solution) was added and the reaction stirred for 1 hour. The THF layer was separated and concentrated in vacuo. The crude oil was purified by column chromatography on silica (25 g), eluting with 100% EtOAc (500 ml) to give N,1-dimethyl-4-nitropyrazole-3-carboxamide, 976 mg.

Workup

  1. stirringthe reaction stirred for 1 hour
  2. customThe THF layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe crude oil was purified by column chromatography on silica (25 g)
  5. washeluting with 100% EtOAc (500 ml)

Sources & evidence

ORD record
ord-5a9192d371c842fdb5bd9853393e7988
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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