Acetic Acid → HCID 12525034, compound

HRID 437734Notes

Reaction equation

HRID 437734 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-])=O)=[CH:4][C:3]=1[C:15]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([CH2:31][CH3:32])([CH3:30])[CH3:29])=[CH:24][C:23]=1[C:33]([CH2:36][CH3:37])([CH3:35])[CH3:34])=[O:16].C(O)(=O)C>O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][C:3]=1[C:15]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([CH2:31][CH3:32])([CH3:29])[CH3:30])=[CH:24][C:23]=1[C:33]([CH2:36][CH3:37])([CH3:35])[CH3:34])=[O:16]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20356579HCID 20356579, compound

Product 1

HCID 12525034HCID 12525034, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g of 1-hydroxy-4-nitro-N-[γ-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamide was reduced using 50 g of reduced iron in 500 ml of a 90% acetic acid aqueous solution. The reaction mixture was poured into water and extracted with ethyl acetate. Then the ethyl acetate was removed by distillation and the residue was recrystallized from ligroin to obtain 40 g of the titled compound. The melting point was 132°-133° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThen the ethyl acetate was removed by distillation
  3. customthe residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-4b2577176f3849289e71270dedbc4be2
Source dataset
uspto-grants-1977_06
Patent number
US04032345

Reaction notes

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