Water → 5-Bromo-1-methyl-3-indolylacetic acid

HRID 863704Notes

Reaction equation

HRID 863704 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][C:14]([OH:16])=[O:15].[CH3:17]I.O>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:17])[CH:8]=[C:7]2[CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 967345-Bromo-3-indoleacetic acid

Product 1

HCID 196964075-Bromo-1-methyl-3-indolylacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg of a 60% dispersion of sodium hydride in mineral oil were added to solution of 1 g of 5-bromoindole-3-acetic acid in 50 ml of tetrahydrofuran and the mixture was stirred under a nitrogen atmosphere for 1 hour. Thereafter, 820 mg (5.8 mmol) of methyl iodide were added and the mixture was stirred under a nitrogen atmosphere for 24 hours. Then, 5 ml of water were added and the solvent was removed under reduced pressure. The residue was treated with 2M hydrochloric acid and the precipitate formed was filtered off, washed with n-hexane and dried. The obtained solid was recrystallized from diethyl ether to give 5-bromo-1-methyl-3-indolylacetic acid of melting point 192°-194° C.

Workup

  1. stirringthe mixture was stirred under a nitrogen atmosphere for 24 hours
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was treated with 2M hydrochloric acid
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with n-hexane
  7. customdried
  8. customThe obtained solid was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-e0de98826901459eb967bedd29d140e1
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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