Hydrochloric Acid → 4,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1891347Notes

Reaction equation

HRID 1891347 reaction equation
[C:1]1([NH:7][C:8](=[O:13])[CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:12][C:10]1([CH3:11])[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[NH:7][C:8](=[O:13])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 123870223-Methyl-N-phenylbut-2-enamide

Product 1

HCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To 3-methyl-but-2-enoic acid phenylamide (7.6 g, 43 mmol) in DCM (100 mL) was added AlCl3 (8.7 g, 65.2 mmol) and the mixture was stirred at 50° C. for 2 hrs. After cooling to rt, the mixture was treated with 1N HCl (50 mL) and extracted with DCM (30 mL×2). This solution was then washed with brine (50 mL×2) and dried over MgSO4. The filtrate was evaporated to afford 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one as a brown solid in quantitative yield (7.6 g). MS: 176.0 (M+H)+; tR=1.91 min (method 1).

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with DCM (30 mL×2)
  3. washThis solution was then washed with brine (50 mL×2)
  4. dry with materialdried over MgSO4
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-04e266ea758c4adb85f3b94382b138f9
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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