3-Chloroaniline → HCID 12588336, compound

HRID 2086777Notes

Reaction equation

HRID 2086777 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 12588336HCID 12588336, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (2.27 g), 3-chloroaniline (1.5 ml) and potassium carbonate (2.2 g) in 1,4-dioxane (30 ml) was refluxed for 20 hours. The insoluble materials were removed by filtration and the filtrate was concentrated. Silica gel column chromatography (chloroform-methanol, 50:1) afforded 2-(3-chlorophenylamino)-3-nitropyridine (404 mg) as an orange solid.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customThe insoluble materials were removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fb6281b8311b44fcbb6c416353affade
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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