HCID 54552579, compound → HCID 54454581, compound

HRID 839061Notes

Reaction equation

HRID 839061 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([N+:20]([O-])=O)[CH:5]=1>C(OCC)(=O)C.[Ni]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([NH2:20])[CH:5]=1

Participants

4

Reactant 1

HCID 54552579HCID 54552579, compound

Product 1

HCID 54454581HCID 54454581, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

25 g of 3,5-dinitro-4-phenoxy-benzoic acid methyl ester are dissolved in 250 ml of ethyl acetate, combined with 10 g of Raney nickel and hydrogenated. After absorption of the calculated amount of hydrogen, the catalyst is filtered off, the solvent is removed, whereupon the remaining oil crystallises. The raw product may be further reacted directly or recrystallized from methanol/water, whereby the diamino ester is obtained in form of colorless crystals melting at 140°-142° C in excellent yield. Alternatively, the hydrogenation may also be carried out in an autoclave at 50° C and 100 atmospheres gauge pressure. The reaction time is then 3 to 5 hours, depending on the reactivity of the Raney nickel.

Workup

  1. customAfter absorption of the calculated amount of hydrogen
  2. filtrationthe catalyst is filtered off
  3. customthe solvent is removed, whereupon the remaining oil
  4. customcrystallises
  5. customThe raw product may be further reacted directly
  6. customrecrystallized from methanol/water, whereby the diamino ester

Sources & evidence

ORD record
ord-000b706739a744309e77e233dc0b6dd4
Source dataset
uspto-grants-1978_06
Patent number
US04093735

Reaction notes

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