Potassium Carbonate → HCID 22724164, compound

HRID 2231003Notes

Reaction equation

HRID 2231003 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([NH:18][C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)=[O:20])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[C:19]([NH:18][C:14]1[CH:13]=[C:12]([NH:11][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=1)=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 16774264HCID 16774264, compound

Product 1

HCID 22724164HCID 22724164, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (0.87 g), N-(3-aminophenyl)-2-naphthalenecarboxamide (1.31 g) and potassium carbonate (1.0 g) in 1,4-dioxane (20 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-(2-naphthoylamino)phenylamino]-3-nitropyridine (961 mg) 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-bf8772787cee47e883202892f2391193
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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