3-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-ol → 3-[(3-Amino-2-chloroquinolin-4-yl)amino]propan-1-ol

HRID 415523Notes

Reaction equation

HRID 415523 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt].C(#N)C>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9]([C:10]=1[NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 866337273-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-ol

Product 1

HCID 866337283-[(3-Amino-2-chloroquinolin-4-yl)amino]propan-1-olYield 96.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

3-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-ol 11.53 g), acetonitrile (110 mL), and 5% platinum on carbon (1.3 g) were added sequentially to a Parr vessel. The vessel was placed under hydrogen pressure, 40 psi (2.8×105 Pa) for 4 hours. The reaction mixture was filtered through a layer of CELITE filter aid and the filtrate was concentrated under reduced pressure. The residue was dried under vacuum for 2 hours to provide 9.97 g of 3-[(3-amino-2-chloroquinolin-4-yl)amino]propan-1-ol as a brown sticky oil.

Workup

  1. customfor 4 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was dried under vacuum for 2 hours

Sources & evidence

ORD record
ord-5c94c807bf8c4132ad6b36ad8f61596c
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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