Reaktion #46321

ord-6743d8ec90324a3ab4a5adaa4a0af75c

Reaktionsgleichung

[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
COc1cc2c(c3c1c(=O)c1cc4ccccc4nc1n3C)C=CC(C)(C)O2
product
COc1cc2c(c3c1c(=O)c1cc4ccccc4nc1n3C)C=CC(C)(C)O2
6-Methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno-[6,5-g][1,8]naphthyridin-7-one
O
water
→
COc1cc2c(c3c1c(=O)c1cc4ccccc4nc1n3C)C(=O)C(O)C(C)(C)O2
expected product
COc1cc2c(c3c1c(=O)c1cc4ccccc4nc1n3C)C(=O)C(O)C(C)(C)O2
2-Hydroxy-6-methoxy-3,3,14-trimethyl-2,3-dihydro-1H-benzo[b]-chromeno[6,5-g][1,8]naphthyridin-1,7(14H)-dione

Edukte

[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
COc1cc2c(c3c1c(=O)c1cc4ccccc4nc1n3C)C=CC(C)(C)O2
product
COc1cc2c(c3c1c(=O)c1cc4ccccc4nc1n3C)C=CC(C)(C)O2
6-Methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno-[6,5-g][1,8]naphthyridin-7-one
O
water

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONOver the course of 30 minutes, add
  2. 2
    Extraktionextraction and treatment

Vorschrift

Over the course of 30 minutes, add a suspension of 1.28 g of KMnO4 in 15 ml of water dropwise to a solution of 0.5 g of the product of Example 2 dissolved in 25 ml of acetone. The reaction mixture is stirred at ambient temperature for 8 hours and then, following conventional extraction and treatment, the expected product is isolated by chromatography of the residue on silica gel (dichloromethane/methanol:98/2).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741325B2uspto-grants-2010_06