Ammonia → beta-Amino-beta-(2-naphthyl)acrylonitrile

HRID 918235노트

반응식

HRID 918235 반응식
[Na].N.[C:3](#[N:5])[CH3:4].[C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)#[N:7]>C(OCC)C>[NH2:7][C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[CH:4][C:3]#[N:5]

참가 물질

6

반응물 4

HCID 222Ammonia2회HCID 6342Acetonitrile2회HCID 119442-NaphthalenecarbonitrileHCID 5360545Sodium

생성물 1

HCID 68142773beta-Amino-beta-(2-naphthyl)acrylonitrile수율 22.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 2.0 grams (0.087 mole) of sodium in 125 milliliters of liquid ammonia was added a solution of 3.67 grams (0.089 mole) of acetonitrile in 10 milliliters of diethyl ether over a period of about five minutes. The reaction mixture was then cooled in a dry ice-acetone bath and a solution of 10.0 grams (0.065 mole) of 2-cyanonaphthalene in a minimum of dry diethyl ether was rapidly added within about five minutes after completion of the acetonitrile addition. The reaction mixture was stirred for about one and one-half hours and the ammonia was then allowed to evaporate. Water was cautiously added to the reaction mixture under nitrogen and the resulting mixture was extracted with diethyl ether. The ether was separated and the residue recrystallized from a mixture of chloroform and hexane. There was obtained 2.8 grams (22% of theoretical) of β-amino-β-(2naphthyl)acrylonitrile, melting point 85°-90°C. By the process described in Dornow et al., Chemische Berichte 82, 254-6 (1949), the β-amino-β-(2-naphthyl)acrylonitrile was hydrolyzed to β-amino-β-(2-naphthyl)acrylamide.

후처리

  1. temperatureThe reaction mixture was then cooled in a dry ice-acetone bath
  2. customto evaporate
  3. additionWater was cautiously added to the reaction mixture under nitrogen
  4. extractionthe resulting mixture was extracted with diethyl ether
  5. customThe ether was separated
  6. customthe residue recrystallized from a mixture of chloroform and hexane

출처 및 근거

ORD 기록
ord-7994beaba9a141138201bbf42dec4bc3
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03970644

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