Potassium Carbonate → HCID 22724355, compound

HRID 2086823Notes

Reaction equation

HRID 2086823 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[NH2:20])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([NH:20][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 27793343-(Cyclopentyloxy)-4-methoxyaniline

Product 1

HCID 22724355HCID 22724355, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (2.17 g), 3-cyclopentyloxy-4-methoxyaniline (2.58 g) and potassium carbonate (2.6 g) in 1,4-dioxane (30 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-cyclopentyloxy-4-methoxyphenyl)amino]-3-nitropyridine (1.35 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-17e3d06dde634ce8ad0248f1e2a309c0
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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