Methyl iodide → 4,5-Dichloro-n-methyl-2-nitroaniline

HRID 1594501Notes

Reaction equation

HRID 1594501 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[H-].[Na+].CI.[C:17]([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH:6][CH3:17])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 811494,5-Dichloro-2-nitroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 2893174,5-Dichloro-n-methyl-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4,5-dichloro-2-nitroaniline (10 mmol, 2.07 g) in DMF (10 mL) was added NaH (12 mmol, 480 mg of 60% suspension in mineral oil) (exothermic, gas evolution). After 15 min MeI (20 mmol, 1.2 mL) was added. The reaction mixture was allowed to stand at ambient temperature for 1 h, then poured into a solution of saturated NaHCO3 and brine, affording the product as an orange precipitate, which was filtered, washed with water and dried in vacuo. 1H NMR (500 MHz, d6-DMSO) δ 8.27 (m, 1H), 8.22 (s, 1H), 7.25 (s, 1H), 2.96 (d, J=4.9 Hz, 3H).

Workup

  1. customaffording the product as an orange precipitate, which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ef3d4c5580814325a6f794fdb3de4805
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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