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

HRID 445158

Reaktionsgleichung

Reaktionsgleichung von HRID 445158
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 21868444Ether tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3953030811ec4672bfe2eb375b1b9c64
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476286B2

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