Acetic Acid → methyl 5-hydroxy-1H-indole-2-carboxylate

HRID 1874787Notes

Reaction equation

HRID 1874787 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.[CH3:14][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:5]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 889585-Hydroxyindole-2-carboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 21904362methyl 5-hydroxy-1H-indole-2-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

5-Hydroxy-1H-indole-2-carboxylic acid (0.50 g, 2.82 mmol) was dissolved in MeOH:CH2Cl2 (1:1, 15 mL), trimethylsilyl diazomethane (2.0 M in hexanes, ˜5.0 mL) was added dropwise until a persistent yellow color formed and the reaction mixture was stirred for 0.5 h. To the solution was added acetic acid (0.5 mL) and the solvent was evaporated. Purification was accomplished by column chromatography (CH2Cl2: MeOH) to afford the title compound (0.55 g, 99%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.59 (br. s., 1H), 8.88 (dd, 1H), 7.23 (d, 1H), 6.85-6.96 (m, 2 H), 6.77 (dd, 1H), 3.81 (d, 3H). MS: m/z 192.2 (M+1).

Workup

  1. customformed
  2. customthe solvent was evaporated
  3. customPurification

Sources & evidence

ORD record
ord-53126013823b428ba573d296d21cc5bf
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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