1-Phenyl-1-propanone → 2-Phenyl-3-methyl-8-methoxyquinoline

HRID 1167176Notes

Reaction equation

HRID 1167176 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)[CH2:13][CH3:14].[OH-].[K+]>C(O)C>[C:16]1([C:12]2[C:13]([CH3:14])=[CH:6][C:5]3[C:4](=[C:3]([O:2][CH3:1])[CH:10]=[CH:9][CH:8]=3)[N:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 14797Potassium HydroxideHCID 139701212-Amino-3-methoxybenzaldehyde

Product 1

HCID 229959242-Phenyl-3-methyl-8-methoxyquinolineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.3 g (101 mol) of 3-methoxy-2-aminobenzaldehyde and 14 ml (105 mol) of propiophenone are dissolved in 400 ml of ethanol. 1.4 g (25 mol) of potassium hydroxide are added to the reaction mixture and the latter is brought to 100° C. for 8 hours. After cooling the reaction medium, the latter is concentrated under vacuum and 200 ml of water are added. A yellow precipitate forms after a few minutes. The medium is filtered and the yellow precipitate is taken up in a mixture of 300 ml of ethyl ether and of 200 ml of a 1N hydrochloric acid solution. The aqueous phase is extracted with 2×100 ml of ethyl ether. Then, after addition of 300 ml of methylene chloride, 100 ml of a 3N sodium hydroxide solution are added to the aqueous phase. The latter is then extracted with 3×200 ml of methylene chloride. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. 21.2 g of 2-phenyl-3-methyl-8-methoxyquinoline are obtained in the form of a pale yellow solid; M.p.=105° C. (Yield: 85%)

Workup

  1. temperatureAfter cooling the reaction medium
  2. concentrationthe latter is concentrated under vacuum and 200 ml of water
  3. additionare added
  4. waitA yellow precipitate forms after a few minutes
  5. filtrationThe medium is filtered
  6. additionthe yellow precipitate is taken up in a mixture of 300 ml of ethyl ether and of 200 ml of a 1N hydrochloric acid solution
  7. extractionThe aqueous phase is extracted with 2×100 ml of ethyl ether
  8. additionThen, after addition of 300 ml of methylene chloride, 100 ml of a 3N sodium hydroxide solution
  9. additionare added to the aqueous phase
  10. extractionThe latter is then extracted with 3×200 ml of methylene chloride
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a1b09d7b159a4ea7a61c38ec6e46e237
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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