HCID 86227722, compound → 2-chloro-N4-(2-fluoro-2-methylpropyl)quinoline-3,4-diamine

HRID 1097584Notes

Reaction equation

HRID 1097584 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][C:17]([F:20])([CH3:19])[CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt].C(#N)C>[Cl:1][C:2]1[C:11]([NH2:12])=[C:10]([NH:15][CH2:16][C:17]([F:20])([CH3:18])[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86227722HCID 86227722, compound

Product 1

HCID 862277242-chloro-N4-(2-fluoro-2-methylpropyl)quinoline-3,4-diamineYield 105.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A Parr vessel was charged sequentially with 2-chloro-N-(2-fluoro-2-methylpropyl)-3-nitroquinolin-4-amine (4.75 g, 15.8 mmol), acetonitrile (50 mL), and 5% platinum on carbon (475 mg) and placed under hydrogen pressure (40 psi, 2.8×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter aid. The filter cake was washed with methanol. The filtrate was concentrated under reduced pressure to provide 4.45 g of 2-chloro-N4-(2-fluoro-2-methylpropyl)quinoline-3,4-diamine as a solid.

Workup

  1. custompressure (40 psi, 2.8×105 Pa) overnight
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washThe filter cake was washed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-04cb94d01aa94a9e893a52707a4d9140
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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