Hydrazine hydrate (1:1) → 2-Amino-6-(2-phenoxyethoxy)benzamide

HRID 259105Notes

Reaction equation

HRID 259105 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]=1[C:6]#[N:7])([O-])=O.[OH2:22].NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]=1[C:6]([NH2:7])=[O:22]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 122648282-Nitro-6-(2-phenoxyethoxy)benzonitrile

Product 1

HCID 122648352-Amino-6-(2-phenoxyethoxy)benzamideYield 50.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

The crystallized 2-nitro-6-(2-phenoxyethoxy)benzonitrile (5.82 g, 0.0205 mole) is stirred in 116 ml absolute ethanol at 50°C. and 3.62 ml (0.0615 mole) 85 percent hydrazine hydrate is added, followed by small scoops of Raney nickel. The temperature is kept at 50°-60°C. while the Raney nickel is added, and after gas evolution and the exotherm ceases, the mixture is filtered through diatomaceous earth. The filter cake is washed with hot ethanol and the filtrate is concentrated, giving 2.804 g of 2-amino-6-(2-phenoxyethoxy)benzamide m.p. 127°-150°C.

Workup

  1. additionis added
  2. filtrationafter gas evolution and the exotherm ceases, the mixture is filtered through diatomaceous earth
  3. washThe filter cake is washed with hot ethanol
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-fb85180ecc0a4cdaa550ece2541aa59e
Source dataset
uspto-grants-1977_07
Patent number
US04036837

Reaction notes

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