Hydrochloric Acid → 6-Fluoro-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1374618Notes

Reaction equation

HRID 1374618 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(Cl)(Cl)Cl>[CH3:13][C:11]1([CH3:12])[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[NH:8][C:9](=[O:14])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5320912-Butenamide, N-(4-fluorophenyl)-3-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 219083086-Fluoro-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9.4 g (48.7 mmol) of 3-methyl-2-butenoic acid-(4-fluorophenyl)amide is heated to 130–140° C. and mixed in portions with 9.6 g (73.5 mmol) of aluminum trichloride. After the addition is completed, the temperature is kept at 80° C. for 30 more minutes. It is allowed to cool to room temperature and carefully treated with 60 ml of ice water. After 150 ml of chloroform is added, the batch is stirred for 15 minutes, acidified with dilute hydrochloric acid and extracted with chloroform (3×150 ml). The combined organic extracts are washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 6.0 g.

Workup

  1. additionAfter the addition
  2. customis kept at 80° C. for 30 more minutes
  3. extractionextracted with chloroform (3×150 ml)
  4. washThe combined organic extracts are washed with saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation in a vacuum
  7. customColumn chromatography on silica gel with hexane-ethyl acetate yields 6.0 g

Sources & evidence

ORD record
ord-41377c7e77c7432995f30e50ab4cd62b
Source dataset
uspto-grants-2007_01
Patent number
US07166592B2

Reaction notes

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