3-Nitroaniline → HCID 22724037, compound

HRID 2086778Notes

Reaction equation

HRID 2086778 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[N+:9]([C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15])([O-:11])=[O:10]>>[NH2:1][C:2]1[C:3]([NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 74233-NitroanilineHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 22724037HCID 22724037, compoundYield 3.1%

Conditions

Temperature
200 °C

Procedure

A mixture of 3-amino-2-chloropyridine (2.57 g) and 3-nitroaniline (2.76 g) was heated at 200° C. for 1 hour. The mixture was cooled and partitioned between aqueous sodium bicarbonate solution and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, concentrated and subjected to silica gel column chromatography (chloroform-methanol, 40:1) to afford 3-amino-2-(3-nitrophenylamino)pyridine (141 mg) as an orange solid.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between aqueous sodium bicarbonate solution and chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40589d5ef15d49b4ba35cf40386d9100
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…