Réaction #40489

Équation de réaction

(6-chloro-1,3,4,9-tetrahydro-β-carbolin-2-yl)-phenyl-methanone

DDQ

THF H2O

→

2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one

Rendement 75.1%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONthe resulting slurry was added to the cooled solids
2. 2
   Températurealso cooled to −78° C.)
3. 3
   Températuregradually warmed to room temperature
4. 4
   workup.STIRRINGstirred an additional two hours
5. 5
   AutreThe reaction was quenched by the addition of 1 N NaOH
6. 6
   Extractionextracted with 3×150 ml EtOAc
7. 7
   LavageThe combined organic layers were washed with 2×100 ml 1 N HCl, 1×100 ml brine
8. 8
   Séchagedried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated

Mode opératoire

(6-chloro-1,3,4,9-tetrahydro-β-carbolin-2-yl)-phenyl-methanone (1.76 g, 5.66 mmol, 1 equiv.) and DDQ (2.31 g, 10.2 mmol, 1.8 equiv.) were mixed as solids and cooled to −78° C. 15 ml of a 9:1 THF/H2O solution was cooled to −78° C. and the resulting slurry was added to the cooled solids followed by an additional 15 ml of THF (also cooled to −78° C.). The deep blue solution was stirred at −78° C. for 2 hours and then gradually warmed to room temperature and stirred an additional two hours. The reaction was quenched by the addition of 1 N NaOH, and extracted with 3×150 ml EtOAc. The combined organic layers were washed with 2×100 ml 1 N HCl, 1×100 ml brine, dried over MgSO4, filtered and concentrated to yield 1.38 g (75%) of 2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one as oily orange solids.

Source