HCID 22010713, compound → HCID 22010886, compound

HRID 323163Notes

Reaction equation

HRID 323163 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:16]([NH:18][C:19]3[CH:43]=[CH:42][C:22]([C:23]([N:25]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=4[O:34]CC4C=CC=CC=4)[CH3:26])=[O:24])=[CH:21][CH:20]=3)=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.O1CCOCC1.[OH-].[Pd+2].[OH-]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([C:16]([NH:18][C:19]3[CH:43]=[CH:42][C:22]([C:23]([N:25]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=4[OH:34])[CH3:26])=[O:24])=[CH:21][CH:20]=3)=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 22010713HCID 22010713, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22010886HCID 22010886, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(4′-nitrobiphenyl-2-carboxamido)-N-(2-benzyloxy-4-methylphenyl)-N-methylbenzamide (430 mg), 20% palladium hydroxide (80 mg) in methanol (20 ml) and 1,4-dioxane (30 ml) was stirred under atmospheric pressure of hydrogen at 30° C. After 5 hours, the reaction mixture was filtered through a bed of Celite, and the solvent was removed by evaporation and the crude product was purified by silica gel column chromatography (SiO2; 30 g, 3% methanol in chloroform) to give 4-(4′-aminobiphenyl-2-carboxamido)-N-(2-hydroxy-4-methylphenyl)-N-methylbenzamide (350 mg) as amorphous.

Workup

  1. filtrationthe reaction mixture was filtered through a bed of Celite
  2. customthe solvent was removed by evaporation
  3. customthe crude product was purified by silica gel column chromatography (SiO2; 30 g, 3% methanol in chloroform)

Sources & evidence

ORD record
ord-eba1564fdb3d4d1a8fd8b9ece1d4eac4
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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