1,3-Dimethyl-4-[(2-nitrophenyl)amino]pyrazole-5-carboxamide → HCID 20549919, compound

HRID 2058604Notes

Reaction equation

HRID 2058604 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)[C:4]([CH3:20])=[N:3]1>C(O)C.[Pd]>[NH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:5]1[C:4]([CH3:20])=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 1

HCID 205498711,3-Dimethyl-4-[(2-nitrophenyl)amino]pyrazole-5-carboxamide

Product 1

HCID 20549919HCID 20549919, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8.6 g of 1,3-dimethyl-4-[(2-nitrophenyl)amino]pyrazole-5-carboxamide in 400 ml of ethanol are hydrogenated over 0.8 g of 10% strength palladium-on-charcoal for 1 hour at 50° C. analogously to Experiment 1. The mixture is filtered; the filtrate is concentrated to dryness, and the residue from evaporation is recrystallized from 160 ml of ethyl acetate and 120 ml of cyclohexane to yield 7.1 g of 4-[(2-aminophenyl)amino]-1,3-dimethylpyrazole-5-carboxamide, mp 182° to 184° C. (dec.).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. customthe residue from evaporation
  4. customis recrystallized from 160 ml of ethyl acetate and 120 ml of cyclohexane

Sources & evidence

ORD record
ord-7f92dae6ca2441bc9f21960a61c05414
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Reaction notes

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