Propionic Acid → 3-Acetyl-4-hydroxy-7,8-dimethylquinolin-2(1H)-one

HRID 1200226Notes

Reaction equation

HRID 1200226 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:14])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20].C(O)(=O)CC>O.C(Cl)CCl>[C:19]([C:3]1[C:4](=[O:14])[NH:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=2[CH3:13])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 547370004-Hydroxy-7,8-dimethylquinolin-2(1H)-one

Product 1

HCID 547345823-Acetyl-4-hydroxy-7,8-dimethylquinolin-2(1H)-oneYield 94%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

10 g of 4-hydroxy-7,8-dimethyl-2-quinolone was added to 60 cc of ethylene dichloride, and 14 g of aluminum chloride was added thereto under stirring at room temperature. The reaction solution was first slurried by the formation of a complex and then became a uniform solution. Then, a solution of a mixture of 5.3 cc of acetyl chloride and 16 cc of ethylene dichloride was dropwise added thereto at room temperature, and the acetylation reaction was conducted at 50° C. for 3 hours. The reaction solution was cooled to room temperature, and 50 cc of water was carefully added for hydrolysis. Then, 5 cc of propionic acid was added thereto, and ethylene dichloride was distilled off together with water under heating, and the mixture was aged at 100° C. for 3 hours under stirring. The slurry was cooled at room temperature and subjected to filtration. The obtained crystals were dried to obtain 11.5 g of 3-acetyl-4-hydroxy-7,8-dimethyl-2-quinolone. Yield was 94%, and the purity was 98% (as analyzed by liquid chromatography). ##STR7##

Workup

  1. additionwas added
  2. additionwas dropwise added
  3. customat room temperature, and the acetylation reaction
  4. temperatureThe reaction solution was cooled to room temperature
  5. distillationethylene dichloride was distilled off together with water
  6. temperatureunder heating
  7. waitthe mixture was aged at 100° C. for 3 hours
  8. stirringunder stirring
  9. temperatureThe slurry was cooled at room temperature
  10. filtrationsubjected to filtration
  11. customThe obtained crystals were dried

Sources & evidence

ORD record
ord-370f3f2bd45346c393efec3d41066b87
Source dataset
uspto-grants-1990_02
Patent number
US04904787

Reaction notes

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