Ethanol → Ethyl 1-methyl-1H-indole-6-carboxylate

HRID 378370

Reaction equation

HRID 378370 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.[CH2:14](O)[CH3:15]>C(Cl)Cl>[CH2:14]([O:12][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][N:2]2[CH3:1])=[CH:6][CH:7]=1)=[O:13])[CH3:15]

Participants

4

Reactant 2

HCID 702EthanolHCID 198192611-Methyl-1H-indole-6-carboxylic acid

Product 1

HCID 53770857Ethyl 1-methyl-1H-indole-6-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.05 g (6.0 mmol) of 1-methyl-1H-indole-6-carboxylic acid in 15 mL of methylene chloride was added to a stirring solution of 1.905 g (10 mmole) of 1-ethyl-3-(3dimethyl-aminopropyl)carbodiimide hydrochloride, 1.20 g (10 mmole) of 4-dirmethylaminopyridine in 20 mL of methylene chloride at room temperature. Ethanol was added and the reaction stirred for 15 h. The reaction mixture was extracted with ethyl acetate, the organic phase was washed with brine and dried on anhydrous magnesium sulfate. Chrorriatographic purification of this material gave 1.08 g (89%) of 1-methyl-1H-indole-6-carboxylic acid ethyl ester as a pale yellow oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. customChrorriatographic purification of this material

Sources & evidence

ORD record
ord-2d756c730e8646349705d48543bdfbb4
Source dataset
uspto-grants-2000_02
Patent number
US06030994

Linked notes

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