Water → 2-[(2E)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]isoindole-1,3-dione

HRID 55993Notes

Reaction equation

HRID 55993 reaction equation
[Cl:1][C:2]1[C:3]([C:12](=[N:25][OH:26])[CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH:33]1([CH2:36]Br)[CH2:35][CH2:34]1.O>CN(C)C=O>[Cl:1][C:2]1[C:3](/[C:12](=[N:25]/[O:26][CH2:36][CH:33]2[CH2:35][CH2:34]2)/[CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 136987055HCID 136987055, compound

Product 1

HCID 1180716692-[(2E)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]isoindole-1,3-dioneYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 300 mg of N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(hydroxyimino)ethyl]phthalimide in 5 ml of N,N-dimethylformamide, 324 mg of potassium carbonate and 158 mg of cyclopropylmethyl bromide were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 5 ml of water and extracted with ethyl acetate (5 ml×3), the resulting organic layers were combined, washed with water and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (with a gradient of from 1:19 to 4:16) as the eluent to obtain 98 mg of the desired product as a pale yellow resinous substance.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (5 ml×3)
  3. washwashed with water
  4. dry with materialdried over saturated aqueous sodium chloride
  5. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.)

Sources & evidence

ORD record
ord-0d5bc9b9fb7e4c42b7e6db2674468224
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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