Hydrazine hydrate (1:1) → HCID 20515462, compound

HRID 1902484Notes

Reaction equation

HRID 1902484 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[C:3]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].O.NN>[Ni].C(O)C>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:4]1[C:5]([CH3:7])=[CH:6][N:2]([CH3:1])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20515465HCID 20515465, compound

Product 1

HCID 20515462HCID 20515462, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent2×

Procedure

A suspension of Raney nickel in ethanol is added to a warm solution (50° C.) of 80 g of ethyl 1,4-dimethyl-3-(2-nitrophenyl)amino-1H-pyrrole-2-carboxylate and 30 ml of hydrazine hydrate in 2 l of ethanol in such portions that a temperature of 70° C. is not exceeded. After 45 minutes nitrogen evolution is no longer observed when Raney nickel is added. The Raney nickel is filtered off hot and is washed with ethanol. After concentration of the filtrate, 58 g (82%) of the title compound of m.p. 90° C. (from isopropanol) are obtained.

Workup

  1. filtrationThe Raney nickel is filtered off hot
  2. washis washed with ethanol

Sources & evidence

ORD record
ord-0fa024eeccf54a1bb9f987e632800f5f
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Reaction notes

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