Hydrochloric Acid → HCID 15086642, compound

HRID 359102Notes

Reaction equation

HRID 359102 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(B)#N.[Na].Cl>C1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrateHCID 101953985CID 101953985

Product 1

HCID 15086642HCID 15086642, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

p-Chloroaniline (4 g), ethyl 2-oxocyclopentanecarboxylate (4.66 ml) and p-toluenesulfonic acid hydrate (0.66 g) were dissolved in benzene (80 ml), and the mixture was subjected to dehydrating condensation reaction under refluxing for 24 hours, and the mixture was allowed to cool. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give an oily product. This oily product was dissolved in absolute methanol (60 ml) and thereto was added sodium cyanoboron hydride (13.2 g) with stirring at room temperature in 10 portions over a period of 11 days. The reaction mixture was cooled with ice and thereto was added conc. hydrochloric acid (21 ml), and the mixture was concentrated under reduced pressure. Water and ethyl acetate were added to the resultant to separate into layers. The organic layer was washed with water 3 tlmes, and concentrated again under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform/methanol [100:1 (v/v)] to give the oily desired product (3.76 g).

Workup

  1. customcondensation reaction
  2. temperatureunder refluxing for 24 hours
  3. temperatureto cool
  4. customThe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give an oily product
  7. temperatureThe reaction mixture was cooled with ice
  8. concentrationthe mixture was concentrated under reduced pressure
  9. additionWater and ethyl acetate were added to the resultant
  10. customto separate into layers
  11. washThe organic layer was washed with water 3 tlmes
  12. concentrationconcentrated again under reduced pressure
  13. washeluted with a mixed solvent of chloroform/methanol [100:1 (v/v)]

Sources & evidence

ORD record
ord-470ac121d6f944fd8c78f1cf75cd98e8
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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