1-Naphthalenecarbonitrile → Naphthalene-1-carboxamidine hydrochloride

HRID 7538

反応式

HRID 7538 の反応式
[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

参加物

7

反応物 3

HCID 68461-NaphthalenecarbonitrileHCID 25517Ammonium ChlorideHCID 16682925Trimethylaluminum

生成物 1

HCID 12301252Naphthalene-1-carboxamidine hydrochloride

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-df7e8f4754984965badaea04cfade0f5
出典データセット
uspto-grants-2006_08
特許番号
US07087605B2

関連ノート

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