3-(2-Fluoro-6-nitrophenyl)propanoic acid → 5-Fluoro-3,4-dihydroquinolin-2(1H)-one

HRID 50858Notes

Reaction equation

HRID 50858 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH2:11][CH2:12][C:13]([OH:15])=O>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:11][CH2:12][C:13](=[O:15])[NH:8]2

Participants

4

Reactant 1

HCID 156914433-(2-Fluoro-6-nitrophenyl)propanoic acid

Product 1

HCID 227369425-Fluoro-3,4-dihydroquinolin-2(1H)-oneYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The suspension of 3-(2-fluoro-6-nitrophenyl)propanoic acid (6.0 g, 28 mmol) and 10% Pd-C (300 mg) in MeOH was hydrogenated under H2 (4 atm) for 3 h. After filtration, the filtrate was concentrated in vacuo to afford 5-Fluoro-3,4-dihydroquinolin-2(1H)-one (4.6 g) as a slightly brown solid. This crude product was used in the next step without further purification.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b40c29e6a78948fdbef5b0ea2d4d3f58
Source dataset
uspto-grants-2004_03
Patent number
US06713490B2

Reaction notes

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