1-Naphthalenecarbonitrile → Naphthalene-1-carboxamidine hydrochloride

HRID 1241490

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 atmosphere, 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-cyano-naphthalene, 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-5cce14ab66ff41abacd992fb80e7f618
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115602B2

Linked notes

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