Malonic Acid → 3-(3-beta-Carbolinyl)acrylic acid

HRID 1982449Notes

Reaction equation

HRID 1982449 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([CH:14]=O)[N:2]=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1>O>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([CH:14]=[CH:17][C:18]([OH:20])=[O:19])[N:2]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 127891449H-pyrido[3,4-b]indole-3-carbaldehyde

Product 1

HCID 539309953-(3-beta-Carbolinyl)acrylic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of beta-carboline-3-carboxaldehyde, 2.0 g of malonic acid, 40 ml of water-free pyridine and 0.1 ml of piperidine is heated in a steam bath for 4 h. The solvent is evacuated in vacuum and after adding 20 ml of 2-propanol, the precipitate is filtered off. 2.3 g of 3-(3-beta-carbolinyl)-acrylic acid with a m.p. of 240°-260° C. (decomposition) is obtained.

Workup

  1. temperatureis heated in a steam bath for 4 h
  2. customThe solvent is evacuated in vacuum
  3. additionafter adding 20 ml of 2-propanol
  4. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-e85c08a1b8214665babd60ace6dc002a
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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