Water → 2-(4-(6-Methyl-3-nitroquinolin-4-ylamino)phenyl)-2-methylpropanenitrile

HRID 476158Notes

Reaction equation

HRID 476158 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[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>[CH3:27][C:23]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=3)[N:5]=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])=[CH:22][CH:21]=1)([CH3:26])[C:24]#[N:25]

Participants

5

Reactant 3

HCID 962WaterHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 66880085HCID 66880085, compound

Product 1

HCID 668808922-(4-(6-Methyl-3-nitroquinolin-4-ylamino)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-6-methyl-3-nitroquinoline (Compound of Preparation H, 660 mg, 2.97 mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (570 mg, 3.56 mmol) were dissolved in acetic acid (10 ml) and stirred for 2 hours. Water was added and the yellow precipitate was filtered off, washed with water, saturated aqueous NaHCO3 and water. The yellow solid was dried to obtain the title compound. Yield: 600 mg (58%); 1H NMR (DMSO-d6, 300 MHz): δ 9.952 (s, 1H,), 9.016 (s, 1H), 8.184 (s, 1H), 7.890-7.918 (d, 1H, J=8.4 Hz), 7.699-7.727 (d, 1H, J=8.4 Hz), 7.421-7.445 (d, 2H, J=7.2 Hz), 7.082-7.108 (d, 2H, J=7.8 Hz), 2.284 (s, 3H), 1.660 (s, 6H); MS: m/z 347 (M+).

Workup

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

Sources & evidence

ORD record
ord-35b3a9a616234d41a6c7569dd26729d7
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

Loading…