p-Fluoronitrobenzene → HCID 23104487, compound

HRID 2054103Notes

Reaction equation

HRID 2054103 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]([OH:18])=[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[C:17]([OH:18])=[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 11430Potassium CarbonateHCID 281142-Amino-3-HydroxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 23104487HCID 23104487, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

0.3 g of 4-fluoronitrobenzene, 0.468 g of 2-amino-3-hydroxypyridine, 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 poured into a water and ice mixture. The aqueous phase was extracted with ethyl acetate. The organic phase was dried over MgSO4 and then evaporated to dryness under vacuum. 0.15 g of 2-[(4-nitrophenyl)amino]pyrid-3-ol (3) was obtained.

Workup

  1. temperatureHeating
  2. temperatureafter cooling to room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-16b3d5afe6de433bae9990e3ca72631a
Source dataset
uspto-grants-2008_02
Patent number
US07329288B2

Reaction notes

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