HCID 69666330, compound → HCID 69666132, compound

HRID 433984Notes

Reaction equation

HRID 433984 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]([CH2:18][CH3:19])[CH2:16][OH:17])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(O)(C)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]([CH2:18][CH3:19])[CH2:16][OH:17])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 69666330HCID 69666330, compound

Product 1

HCID 69666132HCID 69666132, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

(2R)-2-[(3—Nitroquinolin-4-yl)amino]butan-1-ol (238 g), isopropanol (5 L) and catalyst (23.8 g of 5% platinum on carbon) were combined in a stainless steel vessel and hydrogenated at 50 psi (3.5 Kg/cm2) for 16 hours. The reaction mixture was filtered through a layer of Celite® filter agent to remove the catalyst. The filtrate was concentrated under reduced pressure to provide 208.3 g of (2R)-2-[(3-aminoquinolin-4-yl)amino]butan-1-ol as an amber oil. The reaction was run a second time on the same scale.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of Celite®
  2. filtrationfilter agent
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3b21670a1f0431fa35e6b724d49a289
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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