HCID 86227605, compound → HCID 86626305, compound

HRID 1097605Notes

Reaction equation

HRID 1097605 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])=[C:7]([N+:13]([O-])=O)[C:8]([Cl:12])=[N:9]2)=[CH:4][CH:3]=1>[Pt].C(#N)C>[NH2:13][C:7]1[C:8]([Cl:12])=[N:9][C:10]2[C:5]([C:6]=1[NH:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

4

Reactant 1

HCID 86227605HCID 86227605, compound

Product 1

HCID 86626305HCID 86626305, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

Platinum on carbon (0.2 g of 5%) was added to a solution of 1-[(7-bromo-2-chloro-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol (1.94 g, 5.16 mmol) in acetonitrile in a Parr vessel. The mixture was placed under hydrogen pressure (40 psi, 2.8×105 Pa) for two hours and then filtered through a layer of CELITE filter agent. The filter cake was washed with methanol. The filtrate was concentrated under reduced pressure to provide 1.5 g of 1-[(3-amino-7-bromo-2-chloroquinolin-4-yl)amino]-2-methylpropan-2-ol as an oil.

Workup

  1. customfor two hours
  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

Sources & evidence

ORD record
ord-33ed8728d8c348b988064cd5350471f7
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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