Hydrochloric Acid → HCID 14316423, compound

HRID 1357265Notes

Reaction equation

HRID 1357265 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:5][CH3:6].[CH3:16]I.Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([C:7]1[N:8]([CH3:16])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10920996HCID 10920996, compound

Product 1

HCID 14316423HCID 14316423, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil disperson; 1.52 g, 38.0 mmol) was added under nitrogen in portions over 5 minutes to a solution of 2-butyl-1H-indole (5.00 g, 28.9 mmol) in 150 mL of anhydrous DMF at room temperature. After the addition the reaction was stirred at room temperature for 1.25 h. Methyl iodide (3.60 mL, 57.8 mmol) was then added and the reaction stirred at room temperature for 3.5 h. 1 N HCl was added to the reaction until the evolution of gas ceased. The reaction was diluted with ethyl acetate, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-1-methyl-1H-indole (5.70 g, 100%) as a yellow oil, MS m/z: 188 [M+H]+.

Workup

  1. additionAfter the addition the reaction
  2. stirringthe reaction stirred at room temperature for 3.5 h
  3. extractionextracted multiple times with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-62fc7802b61243e78058dd945ead3451
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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