2-(4-((6-Bromo-3-nitroquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile → 2-(4-((3-Amino-6-bromoquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile

HRID 2199271Notes

Reaction equation

HRID 2199271 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=1>CO.[Ni]>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[CH:20][CH:21]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

4

Reactant 1

HCID 426095672-(4-((6-Bromo-3-nitroquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile

Product 1

HCID 426095682-(4-((3-Amino-6-bromoquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

24 g (58.4 mmol) of 2-[4-(6-bromo-3-nitro-quinolin-4-ylamino)-phenyl]-2-methyl-propionitrile (Example 1e) is shacked in 300 ml of MeOH-THE (1:1) under 1.1 bar of H2 in the presence of 8.35 g of Raney-Ni for 1 h. After completion of the reaction, the catalyst is filtered off and the filtrate is evaporated to dryness to give the title compound as a yellow foam. ES-MS: 381, 383 (M+H)+, Br pattern; analytical HPLC: tret=3.21 min (Grad 1).

Workup

  1. customfor 1 h
  2. customAfter completion of the reaction
  3. filtrationthe catalyst is filtered off
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-74ed39a4de1b4863a52b104e7e741e25
Source dataset
uspto-grants-2016_06
Patent number
US09358229B2

Reaction notes

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