4-(2-Phenyl-1H-indol-3-yl)cyclohex-3-ene-1,1-dicarboxylic acid → HCID 13409292, compound

HRID 1980542Notes

Reaction equation

HRID 1980542 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]2[CH2:21][CH2:20][C:19]([C:25]([OH:27])=[O:26])([C:22]([OH:24])=[O:23])[CH2:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]2[CH2:17][CH2:18][C:19]([C:22]([OH:24])=[O:23])([C:25]([OH:27])=[O:26])[CH2:20][CH2:21]2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 134092834-(2-Phenyl-1H-indol-3-yl)cyclohex-3-ene-1,1-dicarboxylic acid

Product 1

HCID 13409292HCID 13409292, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.3 g (0.015 mol) of 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid (Example 2) in 100 mL of ethanol was combined with 1.2 g of 10% palladium-on-carbon catalyst and hydrogenated on a Parr apparatus at room temperature for 3 h. After the catalyst was removed, the solution was concentrated in vacuo to a gum. This gum was crystallized from ether:hexane and then recrystallized three times from ether:hexane to give 4.0 g (74%) of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1,1-dicarboxylic acid, m.p. 196°-197° C.

Workup

  1. customAfter the catalyst was removed
  2. concentrationthe solution was concentrated in vacuo to a gum
  3. customThis gum was crystallized from ether
  4. customhexane and then recrystallized three times from ether

Sources & evidence

ORD record
ord-136ce513e3a74c878c86df4c1d76cf17
Source dataset
uspto-grants-1985_04
Patent number
US04510158

Reaction notes

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