HCID 22010607, compound → HCID 22010923, compound

HRID 323127Notes

Reaction equation

HRID 323127 reaction equation
[CH:1]1([N:6]([C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[C:7]2[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].Cl.CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7]2[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[CH:9][CH:8]=2)=[O:25])=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 22010607HCID 22010607, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22010923HCID 22010923, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-cyclopentyl-N-(4-nitrobenzoyl)-p-anisidine (1.0 g), 10% palladium on carbon (100 mg) and 2 drops of conc. hydrochloric acid in methanol (10 ml) was stirred under 3 atmospheric pressure of hydrogen at ambient temperature. After 4 hours, the reaction mixture was filtered through a bed of Celite, and concentrated to give N-(4-aminobenzoyl)-N-cyclopentyl-p-anisidine (870 mg), which was used directly for the next step without further purification.

Workup

  1. filtrationthe reaction mixture was filtered through a bed of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ee15537c3148958ff6320854724e7c
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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