6-Nitro-2,4-xylidine → HCID 14085195, compound

HRID 1466482Notes

Reaction equation

HRID 1466482 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[N:13]([O-])=O.[Na+]>C(O)(=O)C.[OH-].[NH4+]>[CH3:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1)[NH:9][N:13]=[CH:8]2

Participants

5

Reactant 2

HCID 742196-Nitro-2,4-xylidineHCID 23668193Sodium Nitrite

Product 1

HCID 14085195HCID 14085195, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14923Ammonium HydroxideSolvent

Procedure

4,6-Dimethyl-2-nitro-phenylamine (10.6 g, 64.08 mmol) prepared in Step A was dissolved in acetic acid (150 mL). Sodium nitrite (5.3 g, 76.90 mmol) was added in drops thereto, and the mixture was stirred for 12 h. After completion of the reaction, the reaction mixture was diluted with ammonium hydroxide, extracted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.0 g, Yield 9%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3bb4e4230a2d4b9f833d30f8c1bf844b
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

Loading…