Methyl iodide → 1-Methyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

HRID 518836

Reaktionsgleichung

Reaktionsgleichung von HRID 518836
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[CH:17]=1)([O-:5])=[O:4].I[CH3:19]>CN(C=O)C>[CH3:19][N:15]1[C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:17][C:10]=2[CH2:11][CH2:12][CH2:13][C:14]1=[O:16]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3561757-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Produkt 1

HCID 578538961-Methyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-oneAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

202 mg of NaH (50%) are added to a solution of 771 mg of 7-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 20 ml of DMF. The reaction medium is stirred for 15 minutes and then 583 mg of iodomethane are added. The mixture is stirred for 4 hours at ambient temperature and then run into ice-cold water and extracted with ethyl acetate. The organic phase is washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a heptane/ethyl acetate (80/20 to 50/50) mixture. 275 mg of 1-methyl-7-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are obtained in the form of a yellow solid.

Aufarbeitung

  1. stirringThe mixture is stirred for 4 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 μm), elution

Quellen und Nachweise

ORD-Eintrag
ord-0238aa25307e4c28909a2a906207c8a9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115140B2

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