Hydrochloric Acid → 4-Amino-1-ethyl-3-methyl-1H-pyrazole-5-carboxamide

HRID 2417678Notes

Reaction equation

HRID 2417678 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([N+:11]([O-])=O)[C:5]([CH3:14])=[N:4]1)[CH3:2].Cl>C(O)C.O.[Fe]>[NH2:11][C:6]1[C:5]([CH3:14])=[N:4][N:3]([CH2:1][CH3:2])[C:7]=1[C:8]([NH2:10])=[O:9]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 12148391H-Pyrazole-5-carboxamide, 1-ethyl-3-methyl-4-nitro-

Product 1

HCID 138229264-Amino-1-ethyl-3-methyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 20 g (0.1 mol) of the above amide in 150 ml of ethanol and 30 ml of water containing 3 ml of conc. HCl is stirred under reflux with 25 g of iron powder for three hours and filtered warm using filter-cell. The filtrate is evaporated in vacuo to yield a pink solid, mp 143°-145° C. (from ethyl acetate-pet. ether) of 4-amino-1-ethyl-3-methylpyrazole-5-carboxamide. The reaction of this aminopyrazole with 18 ml acetic anhydride in 250 ml of methylene dichloride gives 18.5 g of N-(1-ethyl-5-carboxamido 3-methylpyrazol-4-yl)acetamide, mp 248°-250° C.

Workup

  1. filtrationfiltered
  2. temperaturewarm
  3. filtrationusing filter-cell
  4. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-ce23fb62d0284d3385dce65af4dce8ac
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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