Diethyl Ether → (1-(6-((2-Hydroxyethyl)(methyl)amino)-2-naphthyl)ethylidene)malononitrile

HRID 713819Notes

Reaction equation

[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:14]([CH2:16][CH2:17][OH:18])[CH3:15])[CH:10]=2)[CH:5]=1)(=O)[CH3:2].[C:19](#[N:23])[CH2:20][C:21]#[N:22].CCOCC>N1C=CC=CC=1>[C:21]([C:20]([C:19]#[N:23])=[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:14]([CH2:16][CH2:17][OH:18])[CH3:15])[CH:10]=2)[CH:5]=1)[CH3:2])#[N:22]

Participants

Conditions

Temperature: 70 °C

Procedure

0.51 g (2.1 mmol) of the third compound 3 is dissolved in 3 mL of dry pyridine to be added with 0.63 g (8.3 mmol) of malononitrile (CH2(CN)2). Reaction is processed under nitrogen to be heated at 70° C. with stirring for 4 hrs. After cooling, 50 mL of ether is added with sufficient stirring, where the part insoluble to ether is abandoned. The ether solution is washed with 50 mL of water. After being dried with anhydrous sodium sulfate and concentrated under reduced pressure, an organic phase is separated and purified by liquid chromatography (SiO2, CHCl3:EtOAc=1:1). Thus, a red solid product, 2-(1,1-dicyanopropen-2-yl)-6-[(2-hydroxyethyl)methylamino]naphthalene 4 (hereinafter referred to as fourth compound 4), is obtained, which has a weight of 0.46 g and a yield of 75.3%.

Workup

customReaction
temperatureAfter cooling
washThe ether solution is washed with 50 mL of water
dry with materialAfter being dried with anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customan organic phase is separated
custompurified by liquid chromatography (SiO2, CHCl3:EtOAc=1:1)

Sources & evidence

ORD record: ord-dfbc1357b43848758c053ad4202569b3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186423B1

Reaction notes

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