1-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanol → 1-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclopropanol 1-{[(3-nitroquinolin-yl)amino]methyl}cyclopropanol

HRID 547327Notes

Reaction equation

HRID 547327 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:19])[CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]>[Pt].C(OCC)(=O)C.CO>[N+:1]([C:4]1[C:5]([NH:14][CH2:15][C:16]2([OH:19])[CH2:18][CH2:17]2)=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:19])[CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 1

HCID 574554091-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanol

Product 1

HCID 672039411-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclopropanol 1-{[(3-nitroquinolin-yl)amino]methyl}cyclopropanol

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopropanol (3.50 g, 13.5 mmol) and 5% platinum on carbon (350 mg) in ethyl acetate (70 mL) and methanol (7 mL) was hydrogenated under 35 psi (2.4×105 Pa) on a Parr apparatus for 3 hours. The mixture was filtered through CELITE filter agent, which was rinsed with ethyl acetate. The filtrate was concentrated under reduced pressure to yield 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopropanol 1-{[(3-nitroquinolin-yl)amino]methyl}cyclopropanol an orange oil that was used immediately in the next step.

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas rinsed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a01477051704c2e8c0bc83926f814e1
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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