N-[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]methanesulfonamide → N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide

HRID 9498Notes

Reaction equation

HRID 9498 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>[Pt].C(#N)C>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][CH2:16][CH2:17][NH:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

4

Reactant 1

HCID 21984316N-[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]methanesulfonamide

Product 1

HCID 21984309N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

An 8 L stainless steel Parr vessel was charged with N-[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]methanesulfonamide (61 g), 5% Pt/C catalyst (6.0 g) and acetonitrile (3 L). The vessel was evacuated, filled with hydrogen (45 psi, 3.1×105 Pa), and shaken at ambient temperature overnight. The reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide.

Workup

  1. customThe vessel was evacuated
  2. additionfilled with hydrogen (45 psi, 3.1×105 Pa)
  3. filtrationThe reaction mixture was filtered through CELITE
  4. filtrationfilter agent
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b33109869e254d76aed04997a8636ff6
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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