Water → (2-Amino-4,5-dimethoxy-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 445158

반응식

HRID 445158 반응식
[Li]CCCC.[CH:6]([C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)([CH3:8])[CH3:7].[NH2:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:18]=1[C:19]#N.[OH2:29]>CCOCC.CCOCC.C1COCC1>[NH2:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:18]=1[C:19]([C:12]1[CH:13]=[CH:14][C:9]([CH:6]([CH3:8])[CH3:7])=[CH:10][CH:11]=1)=[O:29]

참가 물질

7

반응물 4

HCID 962WaterHCID 114621-Bromo-4-isopropylbenzeneHCID 7359672-Amino-4,5-dimethoxybenzonitrileHCID 178418339Butyllithium

생성물 1

HCID 59259172(2-Amino-4,5-dimethoxy-phenyl)-(4-isopropyl-phenyl)-methanone

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 21868444Ether tetrahydrofuran용매

반응 조건

온도
-5 °C

실험 절차

18.8 ml (30 mmol) of BuLi (1.6 M in hexane) is added dropwise to a cooled (−5° C.) solution of 6 g (30 mmol) 4-isopropyl-1-bromobenzene in 25 ml ether. The reaction mixture is stirred for 15 min at −5° C. and one additional hour at rt. After that time the solution is cooled to −5° C. and a solution 1.8 g (10 mmol) 2-amino-4,5-dimethoxybenzonitrile in 20 ml ether/THF (1:1) is added dropwise. After 30 min the reaction mixture is poured slowly into water and extracted with ethyl acetate. The organic layer is dried and evaporated. The crude material is dissolved in 200 ml ether and stirred with 100 ml 2N HCl for one hour. After chromatography (DCM/MeOH 15:1) the product is obtained as yellow oil.

후처리

  1. customat rt
  2. temperatureAfter that time the solution is cooled to −5° C.
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is dried
  5. customevaporated
  6. dissolutionThe crude material is dissolved in 200 ml ether
  7. stirringstirred with 100 ml 2N HCl for one hour
  8. customAfter chromatography (DCM/MeOH 15:1) the product is obtained as yellow oil

출처 및 근거

ORD 기록
ord-3953030811ec4672bfe2eb375b1b9c64
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476286B2

연결된 노트

불러오는 중…