Dimethylformamide → 6-Quinolinamine, N,N,2-trimethyl-

HRID 1642348

Reaktionsgleichung

Reaktionsgleichung von HRID 1642348
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=C(N)[CH:8]=2)[N:3]=1.[H-].[Na+].CI.[CH3:17][N:18]([CH:20]=O)[CH3:19]>O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[C:20]([N:18]([CH3:19])[CH3:17])[CH:6]=[CH:5][C:4]=2[N:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1031482-Methylquinolin-6-amine

Produkt 1

HCID 667256-Quinolinamine, N,N,2-trimethyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 2-methylquinolin-6-amine (2.4 g, 15.2 mmol) and NaH (2.4 g, 60.8 mmol) in DMF (60 mL) was stirred at 40° C. for 3 hrs. Then CH3I (3.8 mL, 60.8 mmol) was added by syringe. The reaction mixture was stirred at 40° C. overnight and then cooled to room temperature. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine and dried over anhydrous Na2SO4. After purified by column chromatography (hexane/EtOAc=25:1), compound 3 was obtained (1.1 g, 39%). MS [M++1]=187, LC-MS: tR=0.775 min.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 40° C. overnight
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter purified by column chromatography (hexane/EtOAc=25:1)

Quellen und Nachweise

ORD-Eintrag
ord-92121f37aee043a080e461ea293485d1
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119660B2

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