Water → HCID 20148855, compound

HRID 569256Notes

Reaction equation

HRID 569256 reaction equation
[OH-:1].[Na+].[CH2:3]([N:10]1[C:14](=O)[CH2:13][CH:12]([CH2:16][C:17]#N)[CH:11]1[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:27]>>[CH2:3]([N:10]1[CH2:14][CH2:13][CH:12]([CH2:16][C:17]([OH:27])=[O:1])[CH:11]1[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20148837HCID 20148837, compound

Product 1

HCID 20148855HCID 20148855, compound

Procedure

To 90 ml of water containing 10 g of sodium hydroxide was added 5.0 g of 1-benzyl-3-cyanomethyl-2-(2,6-dichlorophenyl)pyrrolidin-5-one. The reaction was refluxed 5 hours, cooled, and filtered. Extraction of the aqueous phase with ether followed by addition of ice and acidification with concentrated hydrochloric acid gave a solid which was then triturated with ether to yield beige crystals. Vacuum drying (0.1 Torr) under refluxing toluene for 15 hours followed by recrystallization from ethanol provided upon drying 1.50 g of colorless crystals, m.p. 186°-188°.

Workup

  1. temperatureThe reaction was refluxed 5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionExtraction of the aqueous phase with ether
  5. additionfollowed by addition of ice and acidification with concentrated hydrochloric acid
  6. customgave a solid which
  7. customwas then triturated with ether
  8. customto yield beige crystals
  9. customVacuum drying (0.1 Torr) under refluxing toluene for 15 hours
  10. customfollowed by recrystallization from ethanol
  11. customprovided
  12. dry with materialupon drying 1.50 g of colorless crystals, m.p. 186°-188°

Sources & evidence

ORD record
ord-3f09fc41733647329d35bb4d5935a460
Source dataset
uspto-grants-1988_03
Patent number
US04731457

Reaction notes

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