Tetrahydrofuran → 9-Benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid

HRID 1417470Notes

Reaction equation

HRID 1417470 reaction equation
[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([O:24]CC3C=CC=CC=3)=[O:23])[CH2:17][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.O1CCCC1.[H][H]>[Pd].CO>[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([OH:24])=[O:23])[CH2:17][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

6

Reactant 3

HCID 8028TetrahydrofuranHCID 54294365Benzyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 538804839-Benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acidYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

20 mg of 10% w/w palladium on charcoal was added to a solution of 100 mg of benzyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate, as obtained in Example 51, in 5 ml each of methanol and of tetrahydrofuran. The reaction mixture was stirred for 3 hours under a stream of hydrogen gas at room temperature, filtered to remove the catalyst, and concentrated by evaporation under reduced pressure. The resulting residue was recrystallized from ethyl acetate and hexane, to yield 75 mg of the title compound, melting at 189°-190° C.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe resulting residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-202471c2345c48e799b51c7c796980b9
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

Loading…