Acetic Anhydride → HCID 23313830, compound

HRID 745600Notes

Reaction equation

HRID 745600 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=[O:13])=[CH:6]2.[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[C:15]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[C:7]1[C:12]([OH:14])=[O:13])(=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 204015-Methoxyindole-2-carboxylic acid

Product 1

HCID 23313830HCID 23313830, compound

Procedure

The starting material is prepared as follows: The mixture of 20 g of 5-methoxyindole-2-carboxylic acid (J. Chem. Soc. 1970, 865) and 200 ml of acetic anhydride is refluxed for 2 hours and allowed to cool to room temperature. It is filtered, the filtrate evaporated and the residue is stirred in 300 ml of water. Excess sodium bicarbonate is added, the mixture stirred for 3 hours and then washed with 200 ml of diethyl ether. The aqueous layer is acidified to pH=1 with concentrated hydrochloric acid and filtration yields the 1-acetyl-5-methoxyindole-2-carboxylic acid melting at 173°-175°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 2 hours
  3. filtrationIt is filtered
  4. customthe filtrate evaporated
  5. additionExcess sodium bicarbonate is added
  6. stirringthe mixture stirred for 3 hours
  7. washwashed with 200 ml of diethyl ether
  8. filtrationThe aqueous layer is acidified to pH=1 with concentrated hydrochloric acid and filtration

Sources & evidence

ORD record
ord-0695722984734b3ea719ca6c89f92f86
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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