Hydrochloric Acid → HCID 19097805, compound

HRID 486300Notes

Reaction equation

HRID 486300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]([CH2:13][CH3:14])=[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[C:9]2=[O:22])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24].B.[Na].CO.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][CH3:14])[CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[C:9]2=[O:22])=[CH:4][C:3]=1[C:23]([F:25])([F:26])[F:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19097813HCID 19097813, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19097805HCID 19097805, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14.0 g (36.4 mmol) of 1-(4-chloro-3-trifluoromethylphenyl)-4-ethyl-3-(3-fluorophenyl) -3-pyrroline-2-one synthesized in Example 5 and 1.10 g (29.1 mmol) of sodium boron hydride were dissolved in 120 ml of tetrahydrofuran, and 22 ml of methanol were slowly added to the solution over about 1.5 hours, while the solution was heated under reflux. Reaction was allowed to proceed at the same temperature for further 1 hour, and the reaction mixture was then poured into 1 N hydrochloric acid, followed by extraction with ethyl acetate. The resultant organic layer was washed with water, an aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and n-hexane was then added to the resultant residue to achieve crystallization, followed by recrystallization from ether-n-hexane, thereby obtaining 13.4 g of the desired product in the state of colorless crystals (yield 95%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customReaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resultant organic layer was washed with water
  6. dry with materialan aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure, and n-hexane
  8. additionwas then added to the resultant residue
  9. customcrystallization
  10. customfollowed by recrystallization from ether-n-hexane

Sources & evidence

ORD record
ord-409f7e8b09dd49629ee0226a2940bbd9
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

Loading…