Potassium Hydroxide → HCID 86611483, compound

HRID 910400Notes

Reaction equation

HRID 910400 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].CO[C:8](=[O:33])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:19][C:18]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)=[CH:11][C:10]=1[CH3:32]>CO>[Cl:30][C:28]1[CH:29]=[C:24]([C:18]2([C:20]([F:23])([F:21])[F:22])[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:2][OH:3])=[O:33])=[C:10]([CH3:32])[CH:11]=3)[CH2:19]2)[CH:25]=[C:26]([Cl:31])[CH:27]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59563501Methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoate

Product 1

HCID 86611483HCID 86611483, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
40 °C

Procedure

In a solution of 0.30 g of hydroxylamine hydrochloride in 10 ml of methanol, a solution of 0.65 g of potassium hydroxide in 5 ml of methanol was added, then a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid methyl ester synthesized similarly to Steps 1 to 4 of Synthetic Example 28 in 10 ml of methanol was added, and stirred at 40° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of acetic acid aqueous solution (1:1) was added in the residue, and extracted with ethyl acetate (20 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. Toluene was added in the residue and the remaining acetic acid was distilled off azeotropically to obtain 1.01 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzhydroxamic acid as white crystal.

Workup

  1. additionwas added
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure, 10 ml of acetic acid aqueous solution (1:1)
  4. additionwas added in the residue
  5. extractionextracted with ethyl acetate (20 ml×2)
  6. dry with materialdried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  7. distillationthe solvent was distilled under reduced pressure
  8. additionToluene was added in the residue
  9. distillationthe remaining acetic acid was distilled off azeotropically

Sources & evidence

ORD record
ord-855358a404a14ca8b3925e0d8bb25f5d
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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