Methanol → HCID 13576815, compound

HRID 1905028Notes

Reaction equation

HRID 1905028 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-88bba90d390f448b972b5e9ff4e04f3c
Source dataset
uspto-grants-1989_06
Patent number
US04841056

Reaction notes

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