Acetic Acid → 5-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 250200Notes

Reaction equation

HRID 250200 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:12]=O)=[CH:6][NH:7]2.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:12]=[C:19]1[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]1=[O:18])=[CH:6][NH:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 1462294-Methoxyindole-3-aldehyde

Product 1

HCID 580886345-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dioneYield 49.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-MethoxyIndole-3-carboxaldehyde (5.0 g) and Meldrum's acid (2,2-Dimethyl-[1,3]dioxane-4,6-dione, 4.11 g) were mixed in toluene (200 ml). To this mixture was added 0.6 ml each of piperidine and acetic acid. The reaction mixture was stirred at room temperature for four hours. The precipitate was filtered and washed with toluene to afford 4.25 g of crude 5-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione as an orange solid which was used without further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with toluene

Sources & evidence

ORD record
ord-5ec2ee22f47648618acde918198d5833
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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