HCID 54419371, compound → (3-Indolylethylidene)acetamidomalonic acid

HRID 1457241Notes

Reaction equation

HRID 1457241 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]=[CH:12][C:13]([NH:15][CH:16]([C:27]([O:29]CC2C=CC=CC=2)=[O:28])[C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[O:14])=[CH:2]1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]=[CH:12][C:13]([NH:15][CH:16]([C:27]([OH:29])=[O:28])[C:17]([OH:19])=[O:18])=[O:14])=[CH:2]1

Participants

5

Reactant 2

HCID 54419371HCID 54419371, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54264913(3-Indolylethylidene)acetamidomalonic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

The diester (72) (930 mg, 1.92 mmol), palladium hydroxide on carbon (Pearlman's catalyst) (125 mg) and 95% ethanol (110 mL) were placed in a Parr hydrogenation vessel and subjected to a hydrogen pressure of 45 psi at 25° C. for 3 hours (until the uptake of hydrogen ceased). The reaction mixture was filtered through Celite to remove the catalyst, then evaporated to dryness to give the title compound (73) (576 mg, 99%) which was used without further purification. δ H (300 M Hz; D2O), 1.55 (3H, d, J 7 Hz, CH3), 1.99 (3H, S, CH3CO), 4.09 (1H, brd, J 7 Hz, CH,(CH3), 7.12-7.24 (3H, m), 7.49 (1H, d, J 8 Hz, indole 7-H), 7.71 (1H, d, J 8 Hz, indole 4-H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customto remove the catalyst
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-e0c8d727c18443afb35abb0d9a003b15
Source dataset
uspto-grants-1998_12
Patent number
US05846942

Reaction notes

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