HCID 913632, compound → 6,7-Dimethyl-2(1H)-quinolinone

HRID 2354408Notes

Reaction equation

HRID 2354408 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])/[CH:11]=[CH:12]/C2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Al+3].[Cl-].[Cl-].[Cl-].ClC1C=C2C(=CC=1Cl)N(CC(O)=O)C(=O)C=C2>>[CH3:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[CH3:1])[NH:9][C:10](=[O:19])[CH:11]=[CH:12]2

Participants

4

Reactant 3

HCID 913632HCID 913632, compoundHCID 6451240Aluminum(III) ChlorideHCID 57418656HCID 57418656, compound

Product 1

HCID 106548006,7-Dimethyl-2(1H)-quinolinone

Procedure

A mixture of (2E)-N-(3,4-dimethylphenyl)-3-phenyl-2-propenamide (5.86 g, 23.3 mmol) and AlCl3 (15.6 g, 116.57 mmol) was heated slowly until the mixture became liquefied and then subsequently congealed to form a solid cake. Ice was slowly added to break up the hardened material. The mixture was vigorously stirred for 2 h. The solid material was collected and washed with 2 N HCl solution, water, and ether to obtain a white mixture of product A and B above (3.8 g, 94%), MS (ES) m/e 176 [M+H]+.

Workup

  1. temperaturewas heated slowly until the mixture
  2. customto form a solid cake
  3. additionIce was slowly added
  4. customThe solid material was collected
  5. washwashed with 2 N HCl solution, water, and ether
  6. customto obtain

Sources & evidence

ORD record
ord-8869ccc0e6c14007bea2abcc416e1ca8
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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