Tetrahydrofuran → HCID 68417220, compound

HRID 1800671Notes

Reaction equation

HRID 1800671 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].O1CCCC1>C(O)C.[C].[Pd]>[NH2:18][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:21]=[CH:22][CH:23]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68419705HCID 68419705, compound

Product 1

HCID 68417220HCID 68417220, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-(3-nitrophenyl)benzamide (495 mg, 1.60 mmol) in ethanol (12 mL)/tetrahydrofuran (4 mL) was added 10% palladium-carbon (85 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere (1 atm) for 14 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give N-(3-aminophenyl)-3-(1-cyano-1-methylethyl)benzamide as a pale-brown oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-92113880f09646afba8a8bd682efb31c
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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