8-Nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate → 8-Amino-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate

HRID 520462Notes

Reaction equation

HRID 520462 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([N+:15]([O-])=O)[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:6]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 585528568-Nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate

Product 1

HCID 585528418-Amino-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetateYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C (300 mg) was added to a solution of 8-nitro-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate 38 (2.11 mmol) in ethyl acetate (10 mL). Hydrogen gas was bubbled through the reaction for 10 min, and then the reaction was stirred under 1 atm. hydrogen for 16 h. The catalyst was removed by filtration through 10 g of silica. The solvents were removed in vacuo to give 39 (400 mg, 55% yield for both steps).

Workup

  1. customHydrogen gas was bubbled through the reaction for 10 min
  2. customThe catalyst was removed by filtration through 10 g of silica
  3. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-c0ff502cb7c443bda3240f581e7088e9
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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