Methyl iodide → 5-methoxy-1-methyl-1H-indole-3-carbonitrile

HRID 2165539Notes

Reaction equation

HRID 2165539 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]#[N:13].[H-].[Na+].[H][H].[CH3:18]I>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:18])[CH:7]=[C:6]2[C:12]#[N:13]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 49130085-methoxy-1H-indole-3-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 224772695-methoxy-1-methyl-1H-indole-3-carbonitrileYield 81,307%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-methoxy-1H-indole-3-carbonitrile (550 mg) in dry tetrahydrofuran (50 ml) was treated with NaH (152 mg of a 55% dispersion in oil). The solution was stirred under a dry nitrogen atmosphere until the evolution of hydrogen ceased. Methyl iodide (0.45 mg) was then added and the reaction allowed to stir at room temperature for one hour. The solvent was then removed under reduced pressure and the residue taken up in dichloromethane (50 ml), washed with water (2×25 ml), dried (MgSO4), filtered, and evaporated to dryness under reduced pressure. The residue was recrystallised from absolute ethanol to afford the title compound as white prisms (480 mg); m.p. 105°-108° C.; δH (360 MHz, CDCl3) 3.84 (3H, s, OCH3), 3.87 (3H, s, NCH3), 6.98 (1H, dd, J=7.5, 1.0 Hz, H-6), 7.12 (1H, d, J=1.0 Hz, H-4), 7.31 (1H, d, J=7.5 Hz, H-7), 7.61 (1H, s, H-2); m/z 186 (M+ 100), 171 (90), 143 (80), 116 (20), 101 (15), 89 (15).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. washwashed with water (2×25 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was recrystallised from absolute ethanol

Sources & evidence

ORD record
ord-a9cc6fb6e19948b8836d6ad02ae55d96
Source dataset
uspto-grants-1990_07
Patent number
US04940703

Reaction notes

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