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

HRID 476150Notes

Reaction equation

HRID 476150 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

6-Bromo-4-chloro-3-nitroquinoline (Compound of Preparation A, 18 g, 62.6 mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (Compound of Preparation B, 11 g, 68.9 mmol) was dissolved in acetic acid (350 mL) and the mixture was stirred for 2 hours. Water was added and the yellow precipitate was filtered off. The precipitate was washed with water, saturated aqueous NaHCO3 and water. The yellow solid was dried to obtain the title compound. Yield: 19 g (74%); 1H NMR (DMSO-d6, 300 MHz): δ 10.0 (s, 1H), 8.979 (s, 1H), 8.594 (s, 1H), 7.894-7.926 (d, 1H, J=9.6 Hz), 7.817-7.847 (d, 1H, J=9 Hz), 7.348-7.376 (d, 2H, J=8.4 Hz), 7.011-7.039 (d, 2H, J=8.4 Hz), 1.575 (s, 6H); MS: m/z 409 (M−).

Workup

  1. filtrationthe yellow precipitate was filtered off
  2. washThe precipitate was washed with water, saturated aqueous NaHCO3 and water
  3. customThe yellow solid was dried

Sources & evidence

ORD record
ord-828183deece946eb957ecc17522a7a34
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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