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

HRID 1373883Notes

Reaction equation

HRID 1373883 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>C(O)(C)C.[Pd]>[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

4

Reactant 1

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

Product 1

HCID 21075823tert-butyl N'-(3-aminoquinolin-4-yl)hydrazinecarboxylateYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of tert-butyl N′-(3-nitroquinolin-4-yl)hydrazinecarboxylate (2.50 g, 8.22 mmol) in 150 mL of isopropanol was treated with 1.0 g of 10% palladium on carbon and the mixture was shaken under an atmosphere of hydrogen (3.8×105 Pa) for 2 h. The reaction mixture was then filtered through a pad of CELITE filter agent and rinsed with isopropanol, and the filtrate was concentrated under reduced pressure to give tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (2.18 g) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with isopropanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe49ac0531914bc391effe0326644a53
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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