Methyl iodide → 1-Methyl-1H-indole-6-carboxylic acid

HRID 20980

Reaction equation

HRID 20980 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15]I.[OH-].[K+]>CN(C=O)C.O>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 198192611-Methyl-1H-indole-6-carboxylic acidYield 214.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Reference Example 12, indole-6-carboxylic acid (200 mg, 1.24 mmol) was dissolved in DMF (2 mL), and the solution was treated with 60% sodium hydride-mineral oil dispersant (109 mg, 2.71 mmol), methyl iodide (0.258 mL, 0.410 mmol) and 4 mol/L aqueous potassium hydroxide solution (2 mL). The reaction mixture was added with water and separated into aqueous layer and organic layer, and the organic layer was removed. The aqueous layer was added with 1 mol/L hydrochloric acid to adjust the pH to 1, followed by stirring at room temperature for 1 hour. The obtained solid was collected by filtration and dried under reduced pressure to obtain 1-methylindole-6-carboxylic acid (154 mg, yield 71%).

Workup

  1. customseparated into aqueous layer and organic layer
  2. customthe organic layer was removed
  3. additionThe aqueous layer was added with 1 mol/L hydrochloric acid
  4. filtrationThe obtained solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a5aefe6165594ef5bfe0f2092a468033
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

Loading…