3-chloro-N-(2-fluorophenyl)propanamide → 8-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

HRID 1521628Notes

Reaction equation

HRID 1521628 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[O:9]>>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[NH:10][C:8](=[O:9])[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 42560293-chloro-N-(2-fluorophenyl)propanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Conditions

Temperature
120 °C

Procedure

To a stirred aluminum chloride (26.53 g, 0.199 mol) was added 3-chloro-N-(2-fluorophenyl) propanamide (109-1; 10.0 g, 0.0497 mol). Reaction mass was heated 120° C. and stirred for 5 h. Then reaction mixture was cooled to room temperature and diluted with ice cold water (200 mL) and washed with 17% aqueous hydrochloric acid solution (50 mL) slowly under cooling condition and extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the crude compound which was purified by silica gel column chromatography to obtain the title compound. MS (M+1): 166.1.

Workup

  1. customReaction mass
  2. customThen reaction mixture
  3. temperaturewas cooled to room temperature
  4. washwashed with 17% aqueous hydrochloric acid solution (50 mL) slowly
  5. temperatureunder cooling condition
  6. extractionextracted with ethyl acetate (4×100 mL)
  7. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under vacuum
  10. customto afford the crude compound which
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-087ea4228fc2457599f2f6642d1d5749
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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