Water → HCID 14810857, compound

HRID 1710101Notes

Reaction equation

HRID 1710101 reaction equation
[CH3:1]I.[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[C:13]([OH:15])=[O:14].[OH-].[K+].O>CC(C)=O>[CH3:1][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:3])[C:9]([C:13]([OH:15])=[O:14])=[CH:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 148108567-Methyl-1H-indole-3-carboxylic acid

Product 1

HCID 14810857HCID 14810857, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (30 g) was added to a stirred mixture of 7-methylindole-3-carboxylic acid (4.3 g) and powdered potassium hydroxide (20 g) in anhydrous acetone at 0° C. The resulting suspension was then stirred at room temperature overnight, then poured into water (500 ml), washed with dichloromethane (3×100 ml) and the aqueous phase acidified to pH 2 with hydrochloric acid. The product was isolated by filtration and dried under vacuum to afford white crystals (4.5 g); m.p. 243° C.; δH (360 MHz, DMSO-d6) 2.72 (3H, s, CH3), 4.09 (3H, s, NCH3), 6.92 (1H, d, J=6 Hz, H-6), 7.02 (1H, t, J=6 Hz, H-5), 7.87 (1H, d, J=6, H-4), 7.92 (1H, s, H-2); m/z 189 (M+, 100%), 172 (40), 144 (30), 91 (55).

Workup

  1. washwashed with dichloromethane (3×100 ml)
  2. customThe product was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6d3206ef87ac48f6a5df039528940127
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Reaction notes

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