Methyl iodide → Methyl N-methylindole-6-carboxylate

HRID 1655051Notes

Reaction equation

HRID 1655051 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:16]I>CN(C)C=O.O>[CH3:13][O:12][C:10]([C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][N:1]2[CH3:16])=[CH:5][CH:6]=1)=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 639843Methyl N-methylindole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred solution of methyl 6-indolecarboxylate (5 g) in dry dimethylformamide (30 ml) cooled to 5° C., sodium hydride (60% dispersion in oil, 1.49 g) was added portionwise. The reaction mixture was stirred at 5° C. for 0.5 hour, then a solution of methyliodide (12.18 g) in dry dimethylformamide (10 ml) was added dropwise. After 2 hours, the reaction mixture was diluted with water and the product obtained, after cooling and filtration.

Workup

  1. waitAfter 2 hours
  2. customthe product obtained
  3. temperatureafter cooling
  4. filtrationfiltration

Sources & evidence

ORD record
ord-87e838d64b324cd5b417f1da45d0b814
Source dataset
uspto-grants-1995_04
Patent number
US05410061

Reaction notes

Loading…