Aniline → HCID 3785006, compound

HRID 2353569Notes

Reaction equation

HRID 2353569 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:11][C:4]1[N:3]=[C:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 3785006HCID 3785006, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (386 mg, 2 mmol), aniline (182 μL, 2 mmol) and DIEA(419 μL, 2.4 mmol) in 3 mL dioxane was stirred in microwave at 180° C. for 10 min. After removal of the solvent, the residue was dissolved in 3 mL DCM, subjected to silica gel column purification to give 308 mg (yield 61.7%) (6-chloro-3-nitro-pyridin-2-yl)-phenyl-amine. Calculated mass=249. Observed mass=250.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in 3 mL DCM
  3. customsubjected to silica gel column purification

Sources & evidence

ORD record
ord-d9fd4ce780824a96a38b1ab4a255945d
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

Loading…