m-Toluidine → HCID 22724072, compound

HRID 2230936Notes

Reaction equation

HRID 2230936 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1>C(OCC)(=O)C>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 22724072HCID 22724072, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (1.59 g) and m-toluidine (1.07 g) was heated at 100° C. for 20 minutes. The mixture was cooled and dissolved in ethyl acetate. The organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate, 4:1) to afford 3-nitro-2-[(m-tolyl)amino]pyridine (834 mg) as an orange solid.

Workup

  1. temperatureThe mixture was cooled
  2. washThe organic solution was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0ec7850c1874479993d3f43b1ad1f7f
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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