Methyl iodide → 1-Methyl-6-nitro-2-phenyl-1H-indole

HRID 1896789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896789
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:19]1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].CI>O1CCCC1>[CH3:19][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[C:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 2855718-Crown-6HCID 207598016-Nitro-2-phenyl-1H-indoleHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 214325091-Methyl-6-nitro-2-phenyl-1H-indoleAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-nitro-2-phenyl-1H-indole (106 mg, 0.44 mmol) and 18-Crown-6 (130 mg, 0.49 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature was added potassium tert-butoxide (55 mg, 0.49 mmol) followed by methyl iodide (31 μL, 0.49 mmol). The solution was stirred at room temperature for 30 min. Tetrahydrofuran was removed in vacuo. Ethyl acetate was added, and the organic layer was washed with water and then brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 110 mg (98%) of the title compound.

Aufarbeitung

  1. customTetrahydrofuran was removed in vacuo
  2. additionEthyl acetate was added
  3. washthe organic layer was washed with water
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dfb4c4ff2bbf4ab9a1f5930c4bfab12f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518980B2

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