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

HRID 973071Notes

Reaction equation

HRID 973071 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°-130° 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-12d8bae711494c4cbca86288161f816d
Source dataset
uspto-grants-1977_10
Patent number
US04054666

Reaction notes

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