Hydrochloric Acid → HCID 67163971, compound

HRID 878840Notes

Reaction equation

HRID 878840 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[C:16]([C:24]([CH3:27])([CH3:26])[NH2:25])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[K+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:30])([F:29])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[C:16]([C:24]([CH3:27])([CH3:26])[NH2:25])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67164156HCID 67164156, compound

Product 1

HCID 67163971HCID 67163971, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a solution of 1.35 g of methyl 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(dimethyl-aminomethyl)benzoate in 30 mL of ethanol, a solution of 0.48 g of potassium hydroxide in 15 mL of water was added, and stirred under reflux with heating for 30 minutes. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and 10 mL of 2N hydrochloric acid was added, and the solvent was distilled off under reduced pressure. The residue was dissolved in 20 mL of ethyl acetate, insoluble material was filtered off, and the solvent was distilled off under reduced pressure to obtain 1.05 g of the crude aimed product as white crystal. The resulting product was used as such without purification for the next step.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 30 minutes
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe residue was dissolved in 20 mL of ethyl acetate
  7. filtrationinsoluble material was filtered off
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7d7766dcdeed4a37b68984e748b5131d
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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