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

HRID 1186720Notes

Reaction equation

HRID 1186720 reaction equation
CO.[N+:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])([O-])=O>[Pd].O1CCCC1>[NH2:3][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21]

Participants

5

Reactant 2

HCID 887MethanolHCID 679943233-(1-Nitro-2-naphthylamino)benzonitrile

Product 1

HCID 679939123-(1-Amino-2-naphthylamino)benzonitrileYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a methanol (10 mL) and an anhydrous tetrahydrofuran (50 mL) solution of 3-(1-nitro-2-naphthylamino)benzonitrile (1.60 g, 5.53 mmol) was added 10% palladium-active carbon (160 mg), and the mixture was hydrogenated for 4 hours at room temperature under atmospheric pressure. After removal of the catalyst by filtration, the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to obtain the titled compound as a pale brown powder (1.06 g, yield 74%).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-1e6c6e19951543fdaa272d083fc955ae
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

Loading…