Methanol → Methyl indole-6-carboxylate

HRID 1765604Notes

Reaction equation

HRID 1765604 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:11][C:10]([C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1)=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 639844Methyl indole-6-carboxylate

Procedure

A solution of 1H-indole-6-carboxylic acid (10 g) in methanol (300 mL) was treated with concentrated sulfuric acid (0.5 mL) then heated on a steam bath for 10 hours. The solvent was removed under reduced pressure and the residue partitioned between saturated sodium bicarbonate solution (150 mL) and dichloromethane (150 mL). The aqueous layer was further extracted twice with dichloromethane (150 mL). The combined organics were dried over sodium sulfate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (7:3, v/v) to give the title compound (7.4 g) as a white solid, m.p. 79–81° C. MS: 176(MH+).

Workup

  1. temperaturethen heated on a steam bath for 10 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between saturated sodium bicarbonate solution (150 mL) and dichloromethane (150 mL)
  4. extractionThe aqueous layer was further extracted twice with dichloromethane (150 mL)
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. customthen evaporated
  7. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (7:3

Sources & evidence

ORD record
ord-7d9dc67c776a470fb5e18910226c4c1d
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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