Methyl iodide → 3-(4-Cyano-2-methoxybenzyl)1-methyl-5-nitroindole

HRID 1723232Notes

Reaction equation

HRID 1723232 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[NH:12][CH:11]=2)=[C:7]([O:24][CH3:25])[CH:6]=1)#[N:4].I[CH3:27].[Cl-].[NH4+]>CN(C)C=O>[C:3]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[N:12]([CH3:27])[CH:11]=2)=[C:7]([O:24][CH3:25])[CH:6]=1)#[N:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 233659183-(4-Cyano-2-methoxybenzyl)-5-nitroindole

Product 1

HCID 233658773-(4-Cyano-2-methoxybenzyl)1-methyl-5-nitroindoleYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% w/w dispersion in mineral oil, 0.12 g.) was added to a stirred solution of 3-(4-cyano-2-methoxybenzyl)-5-nitroindole (0.85 g.) in dry N,N-dimethylformamide (10 ml.) under a nitrogen atmosphere. After about one hour, iodomethane (0.645 g.) was added dropwise, and stirring continued at ambient temperature for 5 hours. The mixture was poured onto saturated aqueous ammonium chloride solution, extracted with ethyl acetate (2×20 ml.), the extract washed with water, brine, dried (MgSO4) and evaporated. The residue was crystallized from acetonitrile to give 3-(4-cyano-2-methoxybenzyl)-1-methyl-5-nitroindole (0.72 g., 81%) as a yellow solid, m.p. 200°-201° C.; partial NMR (250 MHz, DMSO-d6): 3.82(s, 3H, NMe); 3.92(s,3H, OMe); 4.12(s,2H, ArCH2).

Workup

  1. waitcontinued at ambient temperature for 5 hours
  2. extractionextracted with ethyl acetate (2×20 ml.)
  3. washthe extract washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-03a6219dd5d24b17a7cd065fc3e9db9c
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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