Ethyl Acetate → HCID 89589794, compound

HRID 925504Notes

Reaction equation

HRID 925504 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:29])([CH3:28])[C:26]#[N:27])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(O)(C)(C)C>[Cl:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:2]2[NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([C:26]#[N:27])([CH3:29])[CH3:28])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 14515789Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 89589794HCID 89589794, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (6.4 g, 23.6 mmol) and 2-(4-aminophenyl)-2-methylpropionitrile (5.6 g, 35 mmol) were dissolved in tert-butanol (200 mL), to the system added potassium carbonate (16.4 g, 119 mmol), and the reaction mixture was stirred under reflux for 2 h. After confirming a disappearance of the raw materials by a thin layer chromatography plate (ethyl acetate:petroleum ether=1:3), the reaction mixture was suction filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether to give 8.1 g of a pale yellow solid.

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washthe resulting residue was washed with diethyl ether

Sources & evidence

ORD record
ord-05cc7c2167ed4f859c8e4f91cecbcb6a
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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