Water → HCID 178440442, compound

HRID 862906Notes

Reaction equation

HRID 862906 reaction equation
[N+:1]([C:4]1[C:5]([CH2:12][CH2:13][CH3:14])=[N:6][NH:7][C:8]=1[C:9]([NH2:11])=[O:10])([O-])=O.[BH4-].[Na+].O>CO.[Pd]>[NH2:1][C:4]1[C:5]([CH2:12][CH2:13][CH3:14])=[N:6][NH:7][C:8]=1[C:9]([NH2:11])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 178440444HCID 178440444, compound

Product 1

HCID 178440442HCID 178440442, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-nitro-3-n-propylpyrazole-5-carboxamide (198 mg, 1.0 mmol ) in methanol (5 ml) was added dropwise to a mixture of sodium borohydride (113 mg, 2.97 mmol), 10% palladium on carbon (5 mg) and water (3 ml). The mixture was stirred at room temperature for 3 hours, filtered and the solvent removed by evaporation under vacuum. Crystallisation of the residue from ethyl acetate-methanol gave the title compound as an off-white solid (61 mg, 36%), m.p. 196°-201° C. Rf 0.4 (silica; dichloromethane, methanol, ammonium hydroxide; 90:10:1). Found: C,48.96; H, 6.98; N,32.08. C7H12N4O requires C,49.98; H, 7.19; N, 33.31%.

Workup

  1. filtrationfiltered
  2. customthe solvent removed by evaporation under vacuum
  3. customCrystallisation of the residue from ethyl acetate-methanol

Sources & evidence

ORD record
ord-c117c392049d46deb16e2c7c586b7aa7
Source dataset
uspto-grants-1998_02
Patent number
US05719283

Reaction notes

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