Beta-Alanine → 2-(3,4-Dihydroxybenzoyl)-3-(5-indolyl)-2-propenenitrile

HRID 1614226Notes

Reaction equation

HRID 1614226 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.[OH:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=1[OH:24])[C:16]([CH2:18][C:19]#[N:20])=[O:17].NCCC(O)=O.O>C(O)C>[OH:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=1[OH:24])[C:16]([C:18](=[CH:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)[C:19]#[N:20])=[O:17]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 962WaterHCID 589040Indole-5-carboxaldehydeHCID 15075591HCID 15075591, compound

Product 1

HCID 3739102-(3,4-Dihydroxybenzoyl)-3-(5-indolyl)-2-propenenitrileYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Formyl indole (145 mg, 1 mmole), 3,4-dihydroxybenzoylacetonitrile (177 mg, 1 mmole) and β-alanine (30 mg) in 30 ml ethanol were refluxed for 3 hours. Water was added and the reaction mixture was extracted with EtOAc. The organic layer was concentrated and the resulting oily residue was purified by chromatography on silica gel to give 86 mg (31%) of the title compound as an orange solid, m.p. 185° C.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. customthe resulting oily residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4d39533788a14e14aa4fe6c53b2685d6
Source dataset
uspto-grants-1993_03
Patent number
US05196446

Reaction notes

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