6-Hydroxy-5-methoxyindole → HCID 19890453, compound

HRID 893547Notes

Reaction equation

HRID 893547 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:11][CH3:12].[CH:13](CC(OC(=O)CC=O)=O)=[O:14]>C1(C)C=CC=CC=1>[CH:13]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[O:11][CH3:12])=[O:14]

Participants

4

Reactant 2

HCID 1270896-Hydroxy-5-methoxyindoleHCID 53941097HCID 53941097, compound

Product 1

HCID 19890453HCID 19890453, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 12 g (0.0735 mole) of 6-hydroxy 5-methoxy indole and 12.95 g (0.147 mole) of formyl acetic anhydride in 100 ml toluene is refluxed for 16 hours under nitrogen atmosphere. After cooling, 30 g of silica 60 is added to the reacting medium, and it is filtered and concentrated to half its volume. The white precipitate that is obtained is filtered and then recrystallized in 30 ml toluene. After vacuum-drying, 4.2 g of 6-formyloxy 5-methoxy indole is obtained (white powder, yield 30%).

Workup

  1. temperatureAfter cooling
  2. addition30 g of silica 60 is added to the reacting medium, and it
  3. filtrationis filtered
  4. concentrationconcentrated to half its volume
  5. customThe white precipitate that is obtained
  6. filtrationis filtered
  7. customrecrystallized in 30 ml toluene
  8. customAfter vacuum-drying

Sources & evidence

ORD record
ord-0733c61ebfb34479b558619fe23cdd40
Source dataset
uspto-grants-1992_06
Patent number
US05126125

Reaction notes

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