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

HRID 1836177Notes

Reaction equation

HRID 1836177 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-380b3fe681444d4c8763ca999d65e541
Source dataset
uspto-grants-2004_08
Patent number
US06777409B2

Reaction notes

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