p-Fluoronitrobenzene → HCID 23104478, compound

HRID 2054109Notes

Reaction equation

HRID 2054109 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[C:17](C)=[CH:16][CH:15]=[CH:14][N:13]=1.[C:19]([O-])([O-])=O.[K+].[K+].CC(C)([O-])C.[K+]>O.CN1CCCC1=O>[CH3:19][C:14]1[N:13]=[C:12]([NH:11][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 153472-Amino-3-methylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 23104478HCID 23104478, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

0.3 g of 4-fluoronitrobenzene, 0.46 g of 2-amino-3-methylpyridine, 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 0.239 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. 0.108 g of 6-methyl-N-(4-nitrophenyl)pyrid-2-amine (9) 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-3520028d897c44b0a2db044c43b40a59
Source dataset
uspto-grants-2008_02
Patent number
US07329288B2

Reaction notes

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