Potassium Carbonate → 2-(3-Iodophenylamino)-3-nitropyridine

HRID 2086791Notes

Reaction equation

HRID 2086791 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[I:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[I: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 11430Potassium CarbonateHCID 122713-IodoanilineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 227244832-(3-Iodophenylamino)-3-nitropyridineYield 21.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (8.5 g), 3-iodoaniline (12.5 g) and potassium carbonate (9.0 g) in 1,4-dioxane (100 ml) was stirred under reflux for 20 hours. After cooling, insoluble materials were removed by filtration and the filtrate was concentrated. The resultant solid was collected and washed with isopropyl ether to give 2-(3-iodophenylamino)-3-nitropyridine (3.88 g) as an orange solid.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureAfter cooling
  3. custominsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-aa96f6c247b04d4d8ff5e66af37f27b9
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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