Methyl iodide → 4-chloro-N-methyl-2-nitroaniline

HRID 1594505Notes

Reaction equation

HRID 1594505 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].CI.[C:16]([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH3:16])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 69794-Chloro-2-nitroanilineHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 27368364-chloro-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-chloro-2-nitroaniline (10 mmol, 1.73 g) in DMF (10 mL) was added portionwise NaH (12 mmol, 480 mg of a 60% suspension in mineral oil) (exothermic, gas evolution). After 10 min MeI (20 mmol, 1.2 mL) was added to the reaction mixture. After 1 h the reaction mixture was poured into aqueous NaHCO3 and brine to afford the product as an orange precipitate, which was filtered, washed with water and dried in vacuo. H1 NMR (500 MHz, d6-DMSO): δ 8.22 (m, 1H), 8.02 (d, J=2.5 Hz, 1H), 7.56 (dd, J=9.1 Hz, 2.5 Hz, 1H), 7.02 (d, J=9.4 Hz, 1H), 2.94 (d, J=5.0 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-3b722b5b418c49f79c88db7529bab26c
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

Loading…