Hydrazine hydrate (1:1) → HCID 20096580, compound

HRID 1769975Notes

Reaction equation

HRID 1769975 reaction equation
O.NN.[CH2:4]([O:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2C(=O)C3=CC=CC=C3C2=O)=[CH:12][C:11]=1[N+:27]([O-:29])=[O:28])=[O:8])[CH3:5]>COCCOC>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([O:6][CH2:4][CH3:5])=[O:8])=[C:11]([N+:27]([O-:29])=[O:28])[CH:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20096586HCID 20096586, compound

Product 1

HCID 20096580HCID 20096580, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

21.0 g (0.42 mol) hydrazine hydrate is added dropwise with stirring under reflux to a suspension of 142.1 g (0.4 mol) 2-ethoxycarbonylamino-5-phthalimido-nitrobenzene in 700 ml 1,2-dimethoxyethane and the mixture is allowed to react for a further 2 hours. After cooling to room temperature, precipitated phthalyl hydrazide is filtered off and the dark red filtrate in the vacuum is evaporated to dryness. The remaining solid residue is recrystallized from about 150 ml toluene. 84.4 g 5-amino-2-ethoxycarbonylaminonitrobenzene are obtained as dark red crystals.

Workup

  1. customto react for a further 2 hours
  2. customprecipitated phthalyl hydrazide
  3. filtrationis filtered off
  4. customthe dark red filtrate in the vacuum is evaporated to dryness
  5. customThe remaining solid residue is recrystallized from about 150 ml toluene

Sources & evidence

ORD record
ord-45b80b347353493b8e33c6cd48395418
Source dataset
uspto-grants-1995_01
Patent number
US05384330

Reaction notes

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