Dimethylformamide → methyl 1-methyl-1H-indole-2-carboxylate

HRID 55482

Reaction equation

[CH3:1]I.N1C2[C:6](=[CH:7][CH:8]=CC=2)[CH:5]=[C:4]1[C:12](O)=O.[C:15](=[O:18])([O-])[O-:16].[K+].[K+].[CH3:21][N:22]([CH3:25])[CH:23]=O>>[CH3:21][N:22]1[C:25]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:12]=[C:23]1[C:15]([O:16][CH3:1])=[O:18]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 72899Indole-2-carboxylic acid

Product 1

HCID 258548methyl 1-methyl-1H-indole-2-carboxylate

Conditions

Temperature: 100 °C

Procedure

6.0 ml of methyl iodide were added dropwise to a mixture of 5.00 g of indole-2-carboxylic acid, 100 ml of dimethylformamide and 13.0 g of anhydrous potassium carbonate, and the resulting mixture was stirred at 100° C. for 6 hours. At the end of this time, the reaction mixture was worked up following the procedure described in Preparation 5, to give 5.12 g of the title compound, melting at 91.3°-92.8° C.

Workup

customdescribed in Preparation 5

Sources & evidence

ORD record: ord-70370978da1647d0b093740de1e756f4
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624935

Linked notes

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