Reaktion #46406

ord-d398ed68e3d64337be7c927a2afc5f77

Reaktionsgleichung

CO.ClCCl
CH2Cl2 methanol
CN(C)CCN1C(=O)c2cccc3cc4cccc(N)c4c(c23)C1=O
11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione
O=C(Cl)CCCCl
4-chlorobutyryl chloride
CN(C)CCN1C(=O)c2cccc3cc4cccc(NC(=O)CCCCl)c4c(c23)C1=O
desired product
Ausbeute 53.0%
CN(C)CCN1C(=O)c2cccc3cc4cccc(NC(=O)CCCCl)c4c(c23)C1=O
4-chloro-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}butanamide
Ausbeute 53.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
20°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent was then evaporated under reduced pressure

Vorschrift

A solution of 100 mg (0.30 mmole) of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) in 4 mL of acetonitrile was stirred at 20° C. 68 μL of 4-chlorobutyryl chloride were added. The mixture was magnetically stirred at 20° C. during 3 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 97:3 volume ratio) to provide 70 mg (yield: 53%) of the desired product (formula below) as an orange powder

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741337B2uspto-grants-2010_06