Methyl iodide → 1-methyl-5-nitro-2-phenyl-1H-indole

HRID 2243081Notes

Reaction equation

HRID 2243081 reaction equation
[H-].[Na+].[C:3]1([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:21]I>CN(C=O)C>[C:3]1([C:9]2[N:10]([CH3:21])[C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=3)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2803095-Nitro-2-phenyl-1H-indole

Product 1

HCID 33992761-methyl-5-nitro-2-phenyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.1 g, 29.0 mmol) is added to 2-phenyl-5-nitro-1H-indole (Example 5b, 6.5 g, 26.0 mmol) in 100 mL of DMF. The mixture is stirred at room temperature for 1 hour. MeI (1.62 mL, 26.0 mmol) is added dropwise and the mixture is stirred at room temperature for 1 hour. The resulting mixture is poured into H2O/ice and the product is filtered off and washed with H2O. The solid is recrystallized from hexane and filtered off. Yield: 6.5 g (99.7%); Rf (2/1 hexane/ethyl acetate): 0.60; IR (KBr): 3434, 2923, 1515, 1462 cm−1; 1H-NMR (d6-DMSO) 8.50 (d, J=1.5 Hz, 1H); 7.90 (dd, J=8.6 Hz, 1.5 Hz, 1H); 7.80-7.30 (m, 6H); 6.75 (s, 1H); 3.75 (s, 3H).

Workup

  1. stirringthe mixture is stirred at room temperature for 1 hour
  2. filtrationthe product is filtered off
  3. washwashed with H2O
  4. customThe solid is recrystallized from hexane
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-bd5e814810694f4981ad8a0ecdf07a12
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

Loading…