1-(7-Bromo-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol → 1-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

HRID 1818129Notes

Reaction equation

HRID 1818129 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C(#N)C.[Pt]>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][CH2:16][C:17]([CH3:18])([OH:19])[CH3:20])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

4

Reactant 1

HCID 219844361-(7-Bromo-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol

Product 1

HCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-olYield 85.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(7-bromo-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol (27.78 g, 81.66 mmol) in acetonitrile (1.2 L) was added to a Parr vessel charged with 5% platinum on carbon (0.84 g), and the reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for two days. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with ethanol (1 L). The filtrate was concentrated under reduced pressure to provide 21.70 g of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol as a yellow oil.

Workup

  1. customfor two days
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with ethanol (1 L)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-80521fb7a9a54b519599ba94ae30551f
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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