tert-butyl N'-(3-nitroquinolin-4-yl)hydrazinecarboxylate → tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylate

HRID 415537Notes

Reaction equation

HRID 415537 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(#N)C.CO>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 1

HCID 21075824tert-butyl N'-(3-nitroquinolin-4-yl)hydrazinecarboxylate

Product 1

HCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl N′-(3-nitroquinolin-4-yl)hydrazinecarboxylate (5.00 g, 16.4 mmol) and 5% platinum on carbon (0.50 g) in acetonitrile (90 mL) and methanol (30 mL) was shaken under hydrogen pressure on a Parr apparatus. When the reaction was complete, the mixture was filtered through a layer of CELITE filter agent. The filter cake was rinsed with 3:1 acetonitrile:methanol. The filtrate was concentrated under reduced pressure to yield 4.50 g of crude tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate as a yellow solid.

Workup

  1. filtrationthe mixture was filtered through a layer of CELITE filter agent
  2. washThe filter cake was rinsed with 3:1 acetonitrile
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a40b39cd6c234336a416eb09a48b8609
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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