Methylamine → 6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 82048

Reaktionsgleichung

Reaktionsgleichung von HRID 82048
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11]Br.[CH3:14][NH2:15]>C1COCC1>[Br:10][C:8]1[CH:9]=[C:4]2[C:5]([CH2:11][N:15]([CH3:14])[C:3]2=[O:2])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Produkt 1

HCID 469420086-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 5-bromo-2-bromomethyl-benzoic acid methyl ester (1.00 g, 3.25 mmol) in THF (6.5 mL) was a solution of methylamine in THF (2M, 8.12 mL, 16.24 mmol). The reaction mixture was heated at 50° C. for 4 hours and then concentrated under vacuum. The residue was taken up in EtOAc and the organic layer was then washed with an aqueous 1M HCl solution, brine, dried (Na2SO4), filtered, concentrated under vacuum to give the title compound (0.73 g, 100%) as a yellow solid.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. washthe organic layer was then washed with an aqueous 1M HCl solution, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6e174c0561454a2d8fc1dd1e6727ca38
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846712B2

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