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

HRID 2090177Notes

Reaction equation

HRID 2090177 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-:14])=[O:13])=[C:5]2Cl.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:19][CH:18]=1.O>C(O)(=O)C>[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-:14])=[O:13])=[C:5]2[NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 219841286-Bromo-4-chloro-3-nitroquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

18 g (62.6 mmol) of 6-bromo-4-chloro-3-nitro-quinoline (Example 1c) and 11 g (68.9 mmol) of (2-(4-amino-phenyl)-2-methyl-propionitrile (Example 1e) are dissolved in 350 ml of acetic acid and stirred for 2 h. After this time, water is added and the yellow precipitate is filtered off and washed with H2O. The solid is dissolved in EtOAc-THF (1:1), washed with sat. aqueous NaHCO3 and dried over MgSO4. The organic phase is evaporated to dryness to give the title compound as a yellow solid. ES-MS: 411, 413 (M+H)+, Br pattern; analytical HPLC: tret=3.69 min (Grad 1).

Workup

  1. filtrationthe yellow precipitate is filtered off
  2. washwashed with H2O
  3. dissolutionThe solid is dissolved in EtOAc-THF (1:1)
  4. washwashed with sat. aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. customThe organic phase is evaporated to dryness

Sources & evidence

ORD record
ord-20af8e0ea2a64ce4a41b8fc717941b7c
Source dataset
uspto-grants-2013_05
Patent number
US08436177B2

Reaction notes

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