Tetrahydrofuran → 3-(1-Amino-2-naphthylamino)benzonitrile

HRID 1260273Notes

Reaction equation

HRID 1260273 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19])([O-])=O.C1COCC1>CO.[C].[Pd]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 679943233-(1-Nitro-2-naphthylamino)benzonitrile

Product 1

HCID 679939123-(1-Amino-2-naphthylamino)benzonitrileYield 93.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-(1-Nitro-2-naphthylamino)benzonitrile (1.16 g, 3.99 mmol) was hydrogenated in methanol (20 mL)/THF (40 mL) for 4 hours at room temperature using 10% palladium-carbon (220 mg) as a catalyst. After removal of the catalyst by filtration, the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatography (chloroform/methanol=99/1), to give the titled compound as a yellow crystal (968 mg, yield 93%).

Workup

  1. customfor 4 hours
  2. customat room temperature
  3. customAfter removal of the catalyst
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=99/1)

Sources & evidence

ORD record
ord-cf945d6418df46979698b355922a891f
Source dataset
uspto-grants-2013_06
Patent number
US08470814B2

Reaction notes

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