Cyanoacetamide → 1,2-Dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrile

HRID 364936노트

반응식

HRID 364936 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]=CN(C)C)[C:9](=O)[CH3:10])=[CH:4][CH:3]=1.[C:17]([CH2:19][C:20]([NH2:22])=[O:21])#[N:18].C[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:19]([C:17]#[N:18])[C:20](=[O:21])[NH:22][C:9]=2[CH3:10])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 867399571-(4-Fluorophenyl)-2-(dimethylamino)ethenyl-2-propanone

생성물 1

HCID 202385991,2-Dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrile수율 90.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-(4-fluorophenyl)-2-(dimethylamino)ethenyl-2-propanone (59.6 grams), cyanoacetamide (26.7 grams) and sodium methoxide (34.3 grams) in 830 ml of dimethylformamide is heated under reflux for two hours and then the reaction mixture is concentrated on a rotary evaporator. The residual solid is suspended in water (2 liters) and is stirred overnight. The aqueous mixture is acidified with 12 N HCl, diluted with water to a volume of 4 liters, and stirred for two hours. The solid product is collected, washed with water (500 ml) and then with ethanol to give 55.4 grams of 1,2-dihydro-5-(4-fluorophenyl)-6-methyl-2-oxo-3-pyridinecarbonitrile.

후처리

  1. temperatureis heated
  2. temperatureunder reflux for two hours
  3. concentrationthe reaction mixture is concentrated on a rotary evaporator
  4. additiondiluted with water to a volume of 4 liters
  5. stirringstirred for two hours
  6. customThe solid product is collected
  7. washwashed with water (500 ml)

출처 및 근거

ORD 기록
ord-4e9a025afcf04fd4b0fae9a40b8a6052
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04607037

반응 노트

불러오는 중…