2-Methyl-3-nitroaniline → HCID 4433548, compound

HRID 1370776Notes

Reaction equation

HRID 1370776 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 117832-Methyl-3-nitroanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 4433548HCID 4433548, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methyl-3-nitroaniline (10.0 g, 65.7 mmoles, purchased from Aldrich) in pyridine (70 mL) was treated with methanesulfonyl chloride (5.09 mL, 65.7 mmoles) at 0° C. The reaction mixture was allowed warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated under reduced pressure and the crude products were diluted with diethyl ether (700 mL). The mixture was washed with 1N HCl (250 mL), water (250 mL) and brine (250 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the title compound which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe crude products were diluted with diethyl ether (700 mL)
  3. washThe mixture was washed with 1N HCl (250 mL), water (250 mL) and brine (250 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63e36e45c746416d9a9499bc0047dad7
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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