HCID 23370079, compound → HCID 23370069, compound

HRID 1901063Notes

Reaction equation

HRID 1901063 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[C:11]2[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]([OH:21])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=2)=[C:5]([N+:27]([O-])=O)[CH:4]=1>C(O)C.[Pd]>[NH2:27][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:26])[C:11]1[CH:16]=[C:15]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:14]([OH:21])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=1

Participants

4

Reactant 1

HCID 23370079HCID 23370079, compound

Product 1

HCID 23370069HCID 23370069, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(4-methoxy-2-nitrophenyl)-3,5-di-t-butyl-4-hydroxybenzamide (1.50 g) in ethanol (10 ml) was added a catalytic amount of 10% palladium/carbon to perform catalytic reduction under a pressure of 1-2.5 arms at room temperature for 5 hrs. After filtering the catalyst and distilling off the solvent, crystallization of the residue from hexane-ethyl acetate afforded N-(2-amino-4-methoxyphenyl)-3,5-di-t-butyl-4-hydroxybenzamide (0.79 g, 57%).

Workup

  1. customat room temperature
  2. customfor 5 hrs
  3. filtrationAfter filtering the catalyst
  4. distillationdistilling off
  5. customthe solvent, crystallization of the residue from hexane-ethyl acetate

Sources & evidence

ORD record
ord-0a9aaa0321944b0b946ede4b986cd19b
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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