HCID 10999447, compound → 2-Phenylquinolin-6-amine

HRID 2243082Notes

Reaction equation

HRID 2243082 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.CO.[Pd]>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 10999447HCID 10999447, compound

Product 1

HCID 171481752-Phenylquinolin-6-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C (10%; 0.60 g) is added to 2-phenyl-6-nitroquinoline (7 g, 0.028 mol) in THF (300 ml) and methanol (300 ml). The mixture is hydrogenated at room temperature and at 1 atm. The catalyst is filtered off, the filtrate is evaporated and the product is recrystallized from isopropyl ether. Yield: 5.7 g (92%); Rf (9/1 chloroform/methanol): 0.56; IR (KBr): 3455, 3320, 3205, 1625, 1495 cm−1.

Workup

  1. customis hydrogenated at room temperature and at 1 atm
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe product is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-30c50a19a791453b89a8ecac714bc420
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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