HCID 66814346, compound → HCID 86227588, compound

HRID 1097602Notes

Reaction equation

HRID 1097602 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Br:19])=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:20]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt].C(#N)C>[CH2:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Br:19])=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66814346HCID 66814346, compound

Product 1

HCID 86227588HCID 86227588, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

Platinum on carbon (1.2 g of 5%) was added to a solution of N-benzyl-7-bromo-3-nitroquinolin-4-amine (10.9 g, 30.4 mmol) in acetonitrile (300 mL) in a Parr vessel. The mixture was placed under hydrogen pressure (30 psi, 2.1×105 Pa) overnight and then filtered through a layer of CELITE filter agent. The filter cake was washed with methanol. The filtrate was concentrated under reduced pressure and further dried for two hours on a vacuum pump to provide 6.33 g of N4-benzyl-7-bromoquinoline-3,4-diamine as a dark green solid.

Workup

  1. custompressure (30 psi, 2.1×105 Pa) overnight
  2. filtrationfiltered through a layer of CELITE filter agent
  3. washThe filter cake was washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customfurther dried for two hours on a vacuum pump

Sources & evidence

ORD record
ord-da3becdc67e044a5a4a6246bf00082d4
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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