HCID 575505, compound → 2-amino-N-naphthalen-1-ylbenzamide

HRID 1266471Notes

Reaction equation

HRID 1266471 reaction equation
[C:1]1([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]([NH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

4

Reactant 1

HCID 575505HCID 575505, compound

Product 1

HCID 8519642-amino-N-naphthalen-1-ylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-naphthyl(2-nitrophenyl)carboxamide in ethanol was added Pd/C and the mixture was stirred under an atmosphere of hydrogen for 16 hours. Pd/C was removed by filtration and the solvent was evaporated. The resulting oil was dissolved in ethyl acetate and extracted with aqueous HCl. The aqueous layer was neutralized and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to give (2-aminophenyl)-N-naphthylcarboxamide, a compound of Formula I.

Workup

  1. customPd/C was removed by filtration
  2. customthe solvent was evaporated
  3. dissolutionThe resulting oil was dissolved in ethyl acetate
  4. extractionextracted with aqueous HCl
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-54040c84f58447f29b1c1e928de9a38a
Source dataset
uspto-grants-2003_04
Patent number
US06548548B2

Reaction notes

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