Ethanol → HCID 178434625, compound

HRID 894116Notes

Reaction equation

HRID 894116 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-])=O)=[C:5]([C:10]([NH2:12])=[O:11])[NH:4][N:3]=1.[CH2:13]([OH:15])C.O>C(O)=O.[Pd]>[CH:13]([NH:7][C:6]1[C:2]([CH3:1])=[N:3][NH:4][C:5]=1[C:10]([NH2:12])=[O:11])=[O:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 178434626HCID 178434626, compound

Product 1

HCID 178434625HCID 178434625, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of 3-methyl-4-nitropyrazole-5-carboxamide (17.0 g, 0.1 mol) in a mixture of 20 ml of 97-100% formic acid, 160 ml of ethanol and 30 ml of water was hydrogenated overnight at 40°-60° using 150 mg of 5% palladium-on-charcoal at 50 psi. Filtration of the hot solution through Celite and evaporation gave 17.8 g of crude, ochre-colored product which was recrystallized from ethanol: 1st crop 9.3 g colorless, 2nd crop 6.7 g brownish, total yield, 16.0 g (95%).

Workup

  1. filtrationFiltration of the hot solution
  2. customthrough Celite and evaporation
  3. customgave 17.8 g of crude, ochre-colored product which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3bdbab5d1cd244b2a8a602a5924a7946
Source dataset
uspto-grants-1981_08
Patent number
US04282361

Reaction notes

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