Methanol → HCID 20356579, compound

HRID 2083560Notes

Reaction equation

HRID 2083560 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH2:28][CH3:29])([CH3:27])[CH3:26])=[CH:21][C:20]=1[C:30]([CH2:33][CH3:34])([CH3:32])[CH3:31])=[O:13].[N+:35]([O-])([OH:37])=[O:36].CO>C(O)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:35]([O-:37])=[O:36])=[CH:4][C:3]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH2:28][CH3:29])([CH3:26])[CH3:27])=[CH:21][C:20]=1[C:30]([CH2:33][CH3:34])([CH3:32])[CH3:31])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 944Nitric AcidHCID 13725190N-[3-[2,4-Bis(1,1-dimethylpropyl)phenoxy]propyl]-1-hydroxy-2-naphthalenecarboxamide

Product 1

HCID 20356579HCID 20356579, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 1 liter of acetic acid, 100 g of 1-hydroxy-N-[γ-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamide was dissolved and nitrated using 23 g of a 60% nitric acid aqueous solution at 15° to 18° C. After the completion of the reaction, 1 liter of methanol was added to the reaction mixture, and the precipitated crystals were filtered and recrystallized from 2 liters of a mixture of ethyl acetate and methanol (2:1 by volume) to provide 70 g of 1-hydroxy-4-nitro-N-[γ-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamide having a melting point of 209° to 210° C.

Workup

  1. customat 15° to 18° C
  2. additionwas added to the reaction mixture
  3. filtrationthe precipitated crystals were filtered
  4. customrecrystallized from 2 liters of a mixture of ethyl acetate and methanol (2:1 by volume)

Sources & evidence

ORD record
ord-84e6b1fb569d4a00a8ea67c255e39683
Source dataset
uspto-grants-1978_04
Patent number
US04086094

Reaction notes

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