Aluminum(III) Chloride → 4,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1440427Notes

Reaction equation

HRID 1440427 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]([CH3:17])=[CH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]>C(Cl)Cl>[CH3:5][C:6]1([CH3:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:8](=[O:9])[CH2:7]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 123870223-Methyl-N-phenylbut-2-enamide2×

Product 1

HCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-oneYield 52.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 500 mL round bottom flask containing AlCl3 (5.22 g, 0.039 mol) was added dry CH2Cl2 (40 mL). Then a solution of N-(3,3-dimethylacryloyl) aniline (Compound 37, 4.45 g, 0.025 mol) in CH2Cl2 (50 mL) was added slowly. The reaction mixture was stirred at room temperature for overnight followed by the addition of ice-cubes. This mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with NaCl (sat.), dried over MgSO4 and concentrated to give a brownish oil. Purification of this oil by column chromatography (10% ethyl acetate in hexane) gave the title compound as a light yellow solid (2.31 g, 52%). 1H NMR d 1.34 (s, 6H), 2.51 (s, 2H), 6.85 (d, J=7.8 Hz, 1H), 7.29 (d, J=7.6 Hz, 1H), 7.03-7.08 (m, 1H), 7.16-7.23 (m, 1H), 9.01 (b, 1H).

Workup

  1. additionfollowed by the addition of ice-cubes
  2. extractionThis mixture was extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic layers were washed with NaCl (sat.)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a brownish oil
  7. customPurification of this oil by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3f6ac72857fa4667bc9b791c41e2aba2
Source dataset
uspto-grants-1996_03
Patent number
US05498755

Reaction notes

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