1-Naphthalenecarbonitrile → Naphthalene-1-carboxamidine hydrochloride

HRID 7538

Reaction equation

[Cl-:1].[NH4+:2].C[Al](C)C.[C:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)#[N:8]>C1(C)C=CC=CC=1.CCCCCC.C(Cl)Cl>[ClH:1].[C:9]1([C:7](=[NH:2])[NH2:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

14 g (261 mmol, 2 equiv.) ammonium chloride are suspended in 150 ml of dry toluene under an argon athmosphere, and the mixture is cooled to 0° C. 130 ml (260 mmol, 2 equiv.) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evolution of gas is observed. After addition of 20 g (130 mmol, 1 equiv.) 1-cyanonaphthalene, the mixture is stirred at 80° C. bath temperature over night. The mixture is cooled and poured into a slurry of silica in methylene chloride. After filtration, the solid is washed with methanol for several times, the solution is evaporated to dryness in vacuo and the residue washed with methanol. The combined filtrates are pooled and stirred in a mixture of methylene chloride containing 10% methanol.

Workup

stirringthe mixture is stirred at 80° C. bath temperature over night
temperatureThe mixture is cooled
filtrationAfter filtration
washthe solid is washed with methanol for several times
customthe solution is evaporated to dryness in vacuo
washthe residue washed with methanol
stirringstirred in a mixture of methylene chloride containing 10% methanol

Sources & evidence

ORD record: ord-df7e8f4754984965badaea04cfade0f5
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Linked notes

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