p-Fluoronitrobenzene → HCID 3137242, compound

HRID 2054113Notes

Reaction equation

HRID 2054113 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:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([CH3:22])[CH:13]=1.C([O-])([O-])=O.[K+].[K+].CN1CCCC1=O>O>[CH3:22][C:14]1[CH: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)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 811164-Amino-2-methylquinoline

Product 1

HCID 3137242HCID 3137242, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.6 g of 4-fluoronitrobenzene, 0.807 g of 4-aminoquinaldine, and 0.705 g of K2CO3 were added to a solution of 2.5 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 6 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. 0.09 g of 2-methyl-N-(4-nitrophenyl)quinol-4-amine (13) was obtained after purification by chromatography on a column of silica (eluent: 50/50 dichloromethane/heptane).

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-dc9dca65f2ba418a8861b93b66760028
Source dataset
uspto-grants-2008_02
Patent number
US07329288B2

Reaction notes

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