Hydrochloric Acid → N-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]phthalimide

HRID 55998Notes

Reaction equation

HRID 55998 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=O)[CH:10]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[CH3:25][O:26][NH2:27].N1C=CC=CC=1.Cl>C(O)C>[Cl:1][C:2]1[C:3]([C:9](=[N:27][O:26][CH3:25])[CH:10]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH3:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 118071579N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl)phthalimide

Product 1

HCID 118071600N-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]phthalimideYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.00 g of N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl]phthalimide in 10 ml of ethanol, 2.39 g of methoxyamine hydrochloride and 3.40 g of pyridine were added and refluxed with heating for 18 hours with stirring. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 30 ml of 1N aqueous hydrochloric acid and extracted with ethyl acetate (40 ml×2). The resulting organic layers were combined, washed with 30 ml of 1N aqueous hydrochloric acid 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 silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 0.81 g of the desired product as a colorless resinous substance.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 18 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (40 ml×2)
  5. washwashed with 30 ml of 1N aqueous hydrochloric acid
  6. dry with materialdried over saturated aqueous sodium chloride
  7. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c713c0af13184af7883e140c14542ade
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

Loading…