1-Naphthalenecarbonitrile → Naphthalene-1-carboxamidine hydrochloride

HRID 1241490

반응식

HRID 1241490 반응식
[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

참가 물질

7

반응물 3

HCID 68461-NaphthalenecarbonitrileHCID 25517Ammonium ChlorideHCID 16682925Trimethylaluminum

생성물 1

HCID 12301252Naphthalene-1-carboxamidine hydrochloride

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5cce14ab66ff41abacd992fb80e7f618
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115602B2

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