Water → 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

HRID 18043Notes

Reaction equation

HRID 18043 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[CH3:7][O:8][C:9]1[C:18]2[C:19](=[O:32])[C:20]3[CH:21]=[C:22]4[CH:31]=[CH:30][CH:29]=[CH:28][C:23]4=[N:24][C:25]=3[N:26]([CH3:27])[C:17]=2[C:16]2[CH:15]=[CH:14][C:13]([CH3:34])([CH3:33])[O:12][C:11]=2[CH:10]=1.[OH2:35]>CC(C)=O>[OH:35][CH:14]1[C:15](=[O:1])[C:16]2[C:17]3[N:26]([CH3:27])[C:25]4[N:24]=[C:23]5[CH:28]=[CH:29][CH:30]=[CH:31][C:22]5=[CH:21][C:20]=4[C:19](=[O:32])[C:18]=3[C:9]([O:8][CH3:7])=[CH:10][C:11]=2[O:12][C:13]1([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 68586536HCID 68586536, compound

Product 1

HCID 685855762-Hydroxy-6-methoxy-3,3,14-trimethyl-2,3-dihydro-1H-benzo[b]-chromeno[6,5-g][1,8]naphthyridin-1,7(14H)-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  1. additionOver the course of 30 minutes, add
  2. extractionextraction and treatment

Sources & evidence

ORD record
ord-6743d8ec90324a3ab4a5adaa4a0af75c
Source dataset
uspto-grants-2010_06
Patent number
US07741325B2

Reaction notes

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