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

HRID 342063Notes

Reaction equation

HRID 342063 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.Cl.[CH2:15](N=C=NCCCN(C)C)[CH3:16].C(O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:15]([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])[CH3:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 198192611-Methyl-1H-indole-6-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1.20 g (10 mmole) of 4-dimethylaminopyridine 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. Chromatographic 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. customChromatographic purification of this material

Sources & evidence

ORD record
ord-24151c348c884256a03b40ffeba6dca5
Source dataset
uspto-grants-1999_01
Patent number
US05856517

Reaction notes

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