HCID 86633711, compound → HCID 86633712, compound

HRID 415454Notes

Reaction equation

HRID 415454 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[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]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86633711HCID 86633711, compound

Product 1

HCID 86633712HCID 86633712, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-3-nitro-N-(pyridin-3-ylmethyl)quinolin-4-amine (13.0 g, 41.0 mmol), 5% platinum on carbon (1.3 g), and acetonitrile (60 mL) were added to a hydrogenation vessel and placed under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. The mixture was filtered through a layer of CELITE filter agent, and the filter cake was washed with acetonitrile and methanol. The filtrate was concentrated under reduced pressure to provide 10.25 g of 2-chloro-N4-(pyridin-3-ylmethyl)quinoline-3,4-diamine, which was used without purification.

Workup

  1. custompressure (50 psi, 3.4×105 Pa) overnight
  2. filtrationThe mixture was filtered through a layer of CELITE filter agent
  3. washthe filter cake was washed with acetonitrile and methanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-69ed652fe89647acba2c93fc83f31185
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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