p-Fluoronitrobenzene → N-(4-Nitrophenyl)pyridin-2-amine

HRID 2054105Notes

Reaction equation

HRID 2054105 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+].CC(C)([O-])C.[K+]>O.CN1CCCC1=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 104392-AminopyridineHCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12695755N-(4-Nitrophenyl)pyridin-2-amineYield 19.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

0.3 g of 4-fluoronitrobenzene, 0.4 g of 2-aminopyridine, and 0.353 g of K2CO3 were added to a solution of 2.5 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 1 hour and 0.286 g of potassium tert-butoxide was then added. Heating was then continued for 6 hours and, after cooling to room temperature, the reaction medium was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 0.09 g of N-(4-nitrophenyl)pyrid-2-amine (5) was obtained.

Workup

  1. temperatureHeating
  2. temperatureafter cooling to room temperature
  3. customThe yellow precipitate formed
  4. filtrationwas filtered off
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-04b152c713f746bd990f3f61d0b4e626
Source dataset
uspto-grants-2008_02
Patent number
US07329288B2

Reaction notes

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