Potassium Carbonate → HCID 66803411, compound

HRID 711389Notes

Reaction equation

HRID 711389 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N: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.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N: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 11430Potassium CarbonateHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 66803305HCID 66803305, compound

Product 1

HCID 66803411HCID 66803411, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A yellow suspension of 6-bromo-4-chloro-3-nitrocinnoline (1.75 g, 6.07 mmol), 2-(4-aminophenyl)-2-methylpropanenitrile (1.069 g, 6.67 mmol) and K2CO3 (1.677 g, 12.13 mmol) in MeCN (2 mL) was heated to reflux for 5 min. The workup followed general workup procedures, and the crude was purified on silica gel with PE/EtOAc as eluant to give 2-(4-(6-bromo-3-nitrocinnolin-4-ylamino)phenyl)-2-methylpropanenitrile as yellow solid (2.5 g, yield 100%). MS (m/z): 414 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 min
  3. customthe crude was purified on silica gel with PE/EtOAc as eluant

Sources & evidence

ORD record
ord-1e452fc4cc6049aeb697b4e98d8dd69b
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

Loading…