Hydrochloric Acid → HCID 67119408, compound

HRID 384834Notes

Reaction equation

HRID 384834 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[CH:7][C:3]=1[C:4]([O-])=[O:5].[C:24]1(C)[C:25](C)=[CH:26]C=[CH:28][CH:29]=1.Cl>[Cl-].[Zn+2].[Cl-].CCC(=O)CC>[CH2:25]([C:24]1[NH:1][C:2]2[C:3]([C:4](=[O:5])[C:29]=1[CH3:28])=[CH:7][C:8]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:23])([F:21])[F:22])=[CH:17][CH:18]=1)=[C:9]([CH3:11])[CH:10]=2)[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7237O-XyleneHCID 86653605HCID 86653605, compound

Product 1

HCID 67119408HCID 67119408, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 7288Ethyl ketoneSolvent

Conditions

Temperature
70 °C

Procedure

2-amino-4-methyl-5-(4-(trifluoromethoxy)phenoxy)benzoate (3.69 g), 20 ml of xylene, 5.3 ml of 3-pentanone, and 0.256 g of zinc chloride were added into a 50-ml glass flask equipped with a stirring device, a thermometer, a reflux condenser, and a Dean-Stark device under a nitrogen atmosphere, and the temperature was raised to reflux with stirring. A reaction was allowed to proceed for 50 hr while adding 1.1 g of zinc chloride in four divided portions. After the completion of the reaction, the mixture was cooled to 70° C., and 10 ml of 0.1 N hydrochloric acid was added to the cooled solution, followed by cooling to room temperature. The precipitated solid was collected on a suction filter, was washed with an aqueous methanol solution and distilled water, and was dried to give 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4(1H)-one as a light brown solid (3.29 g, yield: 87.3%).

Workup

  1. customequipped with a stirring device
  2. temperaturea thermometer, a reflux condenser, and a Dean-Stark device under a nitrogen atmosphere, and the temperature was raised
  3. temperatureto reflux
  4. customAfter the completion of the reaction
  5. temperatureby cooling to room temperature
  6. customThe precipitated solid was collected on a suction
  7. filtrationfilter
  8. washwas washed with an aqueous methanol solution
  9. distillationdistilled water
  10. customwas dried

Sources & evidence

ORD record
ord-36ea1fca4f064646af12a4d2d1208a5d
Source dataset
uspto-grants-2013_02
Patent number
US08367833B2

Reaction notes

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