Hydrochloric Acid → HCID 67119408, compound

HRID 384837Notes

Reaction equation

HRID 384837 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][CH2:6][C:7](=O)[CH2:8][CH3:9].[NH2:11][C:12]1[CH:23]=[C:22]([CH3:24])[C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)=[CH:20][C:13]=1[C:14](OC(C)C)=[O:15].Cl>C1(C)C(C)=CC=CC=1.CO>[CH2:8]([C:7]1[NH:11][C:12]2[C:13]([C:14](=[O:15])[C:6]=1[CH3:5])=[CH:20][C:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([F:35])([F:34])[F:36])=[CH:28][CH:27]=1)=[C:22]([CH3:24])[CH:23]=2)[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7288Ethyl ketone2×HCID 6451240Aluminum(III) Chloride2×HCID 67119420HCID 67119420, compound

Product 1

HCID 67119408HCID 67119408, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent3×

Procedure

Aluminum chloride (30.0 g) and 125 ml of xylene were added into a 1000-ml glass flask equipped with a stirring device, a thermometer, a reflux condenser, and Dean-Stark device under a nitrogen gas stream. 3-Pentanone (58.1 g) was added dropwise thereto with stirring at 10° C. or below. Subsequently, 60.55 g of isopropyl 2-amino-4-methyl-5-(4-(trifluoromethoxy)phenoxy)benzoate dissolved in 250 ml of xylene was added dropwise thereto at room temperature, and the mixture was heated under reflux for 6 hr. A mixture composed of 5.0 g of aluminum chloride, 65 ml of xylene, and 9.69 g of 3-pentanone was added into the reaction solution, and the mixture was further heated under reflux for 18 hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature. The reaction solution was added little by little to 150 ml of a 5% aqueous hydrochloric acid solution prepared in a separate 1000-ml glass flask. Further, 150 ml of methanol was added thereto, and the mixture was heated under reflux for about one hr. The reaction mixture was allowed to cool at room temperature and was collected on a suction filter. The reaction mixture was washed with an aqueous methanol solution and was dried to give 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4(1H)-one as a light brown solid (51.33 g, yield: 90.7%).

Workup

  1. customequipped with a stirring device
  2. additionwas added dropwise
  3. temperatureunder reflux for 6 hr
  4. additionwas added into the reaction solution
  5. temperaturethe mixture was further heated
  6. temperatureunder reflux for 18 hr
  7. customAfter the completion of the reaction
  8. temperatureto cool at room temperature
  9. customprepared in a separate 1000-ml glass flask
  10. temperaturethe mixture was heated
  11. temperatureunder reflux for about one hr
  12. temperatureto cool at room temperature
  13. customwas collected on a suction
  14. filtrationfilter
  15. washThe reaction mixture was washed with an aqueous methanol solution
  16. customwas dried

Sources & evidence

ORD record
ord-432e8124bd244ebab83d68313b7da831
Source dataset
uspto-grants-2013_02
Patent number
US08367833B2

Reaction notes

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