Methyl iodide → 4-Chloro-2-methoxy-N-methyl-6-nitrobenzenamine

HRID 1594526Notes

Reaction equation

HRID 1594526 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([O:12][CH3:13])[CH:3]=1.[H-].[Na+].CI.[C:18]([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH:6][CH3:18])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 59644362HCID 59644362, compound

Product 1

HCID 688782324-Chloro-2-methoxy-N-methyl-6-nitrobenzenamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To the title compound of Example 21, Step B (19.9 mmol, 4.03 g) in DMF (50 mL) at 0° C. was added portionwise NaH (31.8 mmol, 1.27 g of 60% suspension in mineral oil) (exothermic, gas evolution). After 10 min MeI (23 mmol, 1.5 mL) was added and the reaction was allowed to stand at ambient temperature for 3 h. Saturated NaHCO3 and brine were added to the reaction resulting in formation of a precipitate, which was filtered, washed with water and dried in vacuo. Flash chromatography on silica eluting with 15% EtOAc in hexanes afforded the product as a bright red solid. LC-MS (ESI, Method B): 2.31 min, m/z 217.2 (M+1).

Workup

  1. customresulting in formation of a precipitate, which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-deff5b3740fe4b8dade20ab1f2c019d8
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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