p-Fluoronitrobenzene → HCID 23104488, compound

HRID 2054111Notes

Reaction equation

HRID 2054111 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:21]=[CH:20][C:19]2[C:14](=[C:15]([OH:22])[CH:16]=[CH:17][CH:18]=2)[N:13]=1.C([O-])([O-])=O.[K+].[K+].CN1CCCC1=O>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[C:15]([OH:22])[CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 46537882-Amino-8-quinolinol

Product 1

HCID 23104488HCID 23104488, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.3 g of 4-fluoronitrobenzene, 0.683 g of 2-amino-8-hydroxyquinoline, 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 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 0.45 g of 2-[(4-nitrophenyl)amino]quinol-8-ol (11) was obtained.

Workup

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

Sources & evidence

ORD record
ord-5c68529e19704848bd1d10631336d12f
Source dataset
uspto-grants-2008_02
Patent number
US07329288B2

Reaction notes

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