Acetic Acid → Naphthalene-2-carboxamide

HRID 2083561Notes

Reaction equation

HRID 2083561 reaction equation
C(O)(=O)C.O[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([N+]([O-])=O)=[CH:8][C:7]=1[C:19]([NH:21]CCCOC1C=CC(C(CC)(C)C)=CC=1C(CC)(C)C)=[O:20]>[Fe].O>[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[C:19]([NH2:21])=[O:20]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 20356579HCID 20356579, compound

Product 1

HCID 75245Naphthalene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

In 500 ml of a 90% acetic acid aqueous solution, 50 g of 1-hydroxy-4-nitro-N-[γ-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamide was reduced with 50 g of iron as a reducing agent. The reaction mixture was added to water and then was extracted with ethyl acetate. After evaporating off the ethyl acetate, the crystals were recrystallized from ligroin to provide 40 g of 1-hydroxy-4-amino-N-[γ-2,4-di-tert-amylphenoxy)propyl]-2-naphthamide having a melting point of 132° to 133° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customAfter evaporating off the ethyl acetate
  3. customthe crystals were recrystallized from ligroin

Sources & evidence

ORD record
ord-95da9b2771734a05956ca70091cf8a17
Source dataset
uspto-grants-1978_04
Patent number
US04086094

Reaction notes

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