HCID 18791672, compound → HCID 18791356, compound

HRID 1005596Notes

Reaction equation

HRID 1005596 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][CH:38]=[CH:37][C:5]=1[C:6]([NH:8][C:9]1[CH:36]=[CH:35][C:12]([C:13]([N:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:16])=[O:14])=[CH:11][CH:10]=1)=[O:7])([O-])=O.[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:1][C:4]1[CH:40]=[CH:39][CH:38]=[CH:37][C:5]=1[C:6]([NH:8][C:9]1[CH:36]=[CH:35][C:12]([C:13]([N:15]([CH3:16])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:14])=[CH:11][CH:10]=1)=[O:7]

Participants

5

Reactant 2

HCID 18791672HCID 18791672, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18791356HCID 18791356, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(2-nitrobenzoyl)amino-N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (800 mg), 20% palladium hydroxide (200 mg) in ethanol (20 ml) was stirred under atmospheric pressure of hydrogen at ambient temperature. After 2 hours, the reaction mixture was filtered through a bed of Celite, and the solvent was removed by rotary evaporation and the crude product was purified by silica gel column chromatography (SiO2 30 g, ethyl acetate/hexane=3/1) to give 4-(2-aminobenzoyl)amino-N-methyl-N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]benzamide (700 mg).

Workup

  1. filtrationthe reaction mixture was filtered through a bed of Celite
  2. customthe solvent was removed by rotary evaporation
  3. customthe crude product was purified by silica gel column chromatography (SiO2 30 g, ethyl acetate/hexane=3/1)

Sources & evidence

ORD record
ord-c88eb77f1d9c48e399d2f6cb83db7a79
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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