Acetic-formic anhydride → HCID 19890453, compound

HRID 620653Notes

Reaction equation

HRID 620653 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](OC(=O)C)=[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 75269Acetic-formic anhydrideHCID 1270896-Hydroxy-5-methoxyindole

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-methoxyindole and 12.95 g (0.147 mole) of acetic formic anhydride in 100 ml of toluene is brought to reflux for 16 hours under nitrogen. After the mixture is cooled, 30 g of silica 60 are added to the reaction medium, the mixture is filtered and the filtrate concentrated two-fold. The white precipitate obtained is filtered off and then recrystallized again in 30 ml of toluene. After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained.

Workup

  1. temperatureto reflux for 16 hours under nitrogen
  2. temperatureAfter the mixture is cooled
  3. addition30 g of silica 60 are added to the reaction medium
  4. filtrationthe mixture is filtered
  5. concentrationthe filtrate concentrated two-fold
  6. customThe white precipitate obtained
  7. filtrationis filtered off
  8. customrecrystallized again in 30 ml of toluene
  9. customAfter being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield)
  10. customare obtained

Sources & evidence

ORD record
ord-41508f4a810148569fac2dbb6381c36b
Source dataset
uspto-grants-1989_04
Patent number
US04822375

Reaction notes

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