Methanol → HCID 13576815, compound

HRID 1252173Notes

Reaction equation

HRID 1252173 reaction equation
[CH3:1][N:2]1[CH:6]2[CH2:7][C:8]3[C:16]4[C:15]([CH:5]2[CH:4]([C:17]([OH:19])=[O:18])[CH2:3]1)=[CH:14][CH:13]=[CH:12][C:11]=4[NH:10][CH:9]=3.S(=O)(=O)(O)O.[CH3:25]O>>[C:17]([CH:4]1[CH:5]2[CH:6]([CH2:7][C:8]3[C:16]4[C:15]2=[CH:14][CH:13]=[CH:12][C:11]=4[NH:10][CH:9]=3)[N:2]([CH3:1])[CH2:3]1)([O:19][CH3:25])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric Acid2×HCID 13576811HCID 13576811, compound

Product 1

HCID 13576815HCID 13576815, compound

Procedure

To a solution of the free indole 9-carboxylic acid (Example 13) (0.203 g) in methanol (5 cm3) was added with stirring concentrated sulphuric acid (0.15 cm3) and the reaction heated to reflux. After 2 hours further concentrated sulphuric acid (0.1 cm3) was added, reaction was indicated to be complete after 15 hours. The resultant solution was allowed to cool to room temperature to give after evaporation under vacuum and trituration with chloroform a dark orange solid (0.329 g).

Workup

  1. temperaturethe reaction heated to reflux
  2. customreaction
  3. customto give
  4. customafter evaporation under vacuum and trituration with chloroform a dark orange solid (0.329 g)

Sources & evidence

ORD record
ord-2aa524e077a040a9a6345e13d4af4166
Source dataset
uspto-grants-1988_05
Patent number
US04742075

Reaction notes

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