HCID 21548301, compound → HCID 20386599, compound

HRID 1605086Notes

Reaction equation

HRID 1605086 reaction equation
[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22]([O:24]CC3C=CC=CC=3)=[O:23])[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22]([OH:24])=[O:23])[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21548301HCID 21548301, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20386599HCID 20386599, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.6 g. benzyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate in 250 ml. ethyl alcohol containing 0.5 g. 10% palladium-on-charcoal was subjected to a hydrogen atmosphere at 40 p.s.i., while being heated with an infrared lamp and agitated, until uptake of hydrogen ceased. The mixture was filtered, the filtrate was evaporated to dryness under reduced pressure, the resulting residue was dissolved in ether, the ether solution was extracted with dilute potassium bicarbonate, the bicarbonate extract was acidified with 3N-hydrochloric acid and extracted with ether and the ether extract was dried and evaporated to dryness. The resulting residue was crystallized from ether-pentane and a solution of the resulting crystals in 5% potassium bicarbonate solution was acidified with 3N hydrochloric acid and the resulting solid was filtered and washed with water to give 1.3 g. of the title compound; m.p. 70°-80°C.

Workup

  1. temperature, while being heated with an infrared lamp
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. dissolutionthe resulting residue was dissolved in ether
  5. extractionthe ether solution was extracted with dilute potassium bicarbonate
  6. extractionthe bicarbonate extract
  7. extractionextracted with ether
  8. extractionthe ether extract
  9. customwas dried
  10. customevaporated to dryness
  11. customThe resulting residue was crystallized from ether-pentane
  12. filtrationthe resulting solid was filtered
  13. washwashed with water
  14. customto give 1.3 g

Sources & evidence

ORD record
ord-238c9c7babfa429da04441feb4d2237f
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

Loading…