Reaktion #652137

Reaktionsgleichung

2,6-dichloro-3-nitrobenzyl methanesulfonate

8-tert-butoxycarbonylamino-2-methylquinoline

sodium hydride

→

8-[N-tert-butoxycarbonyl-N-(2,6-dichloro-3-nitrobenzyl)amino]-2-methylquinoline

Ausbeute 76.2%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Temperaturcooling
3. 3
   workup.STIRRINGthe mixture was stirred for 80 minutes at the same temperature
4. 4
   workup.WAITfor 15 minutes at ambient temperature
5. 5
   SonstigeThe reaction mixture was partitioned between ethyl acetate and water
6. 6
   TrocknenThe organic layer was dried over magnesium sulfate
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by flash chromatography
9. 9
   Wascheneluting with methylene chloride
10. 10
    Sonstigecrystallized with n-hexane

Vorschrift

To a solution of 8-tert-butoxycarbonylamino-2-methylquinoline (258 mg) in N,N-dimethylformamide (3 ml) was added sodium hydride (44 mg) in an ice-water bath cooling, and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added 2,6-dichloro-3-nitrobenzyl methanesulfonate (300 mg) in an ice water bath cooling, and the mixture was stirred for 80 minutes at the same temperature and then for 15 minutes at ambient temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography eluting with methylene chloride, and crystallized with n-hexane to give 8-[N-tert-butoxycarbonyl-N-(2,6-dichloro-3-nitrobenzyl)amino]-2-methylquinoline (352 mg).

Quelle