HCID 21075826, compound → HCID 21075822, compound

HRID 1373948Notes

Reaction equation

HRID 1373948 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C(#N)C.CO.[Pt]>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

5

Reactant 1

HCID 21075826HCID 21075826, compound

Product 1

HCID 21075822HCID 21075822, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of tert-butyl N′-(7-bromo-3-nitroquinolin-4-yl)hydrazinecarboxylate (50.0 g, 131 mmol) in 320 mL of acetonitrile (MeCN) and 80 mL of methanol was treated with platinum on carbon (5.0 g, 1.3 mmol, 5% w/w) and shaken under an atmosphere of hydrogen (3.8×105 Pa). After 4 h, the reaction mixture was filtered through a pad of CELITE filter agent and rinsed with portions of MeCN:MeOH (1:1) until the filtrate ran clear. The filtrate was concentrated under reduced pressure to yield 37.1 g of tert-butyl N′-(3-amino-7-bromoquinolin-4-yl)hydrazinecarboxylate as a tan solid.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with portions of MeCN:MeOH (1:1) until the filtrate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-94139fffc605480c85eb39334c5400ca
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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