Methanol → 9,10-Dihydro-7-methyl-9-oxo-3-acridinecarboxylic Acid, Methyl Ester

HRID 970323Notes

Reaction equation

HRID 970323 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[CH:8]=[C:9]([C:17]([OH:19])=[O:18])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[CH3:20]O>OS(O)(=O)=O.CN(C=O)C>[CH3:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 685635949,10-Dihydro-7-methyl-9-oxo-3-acridinecarboxylic Acid

Product 1

HCID 865914219,10-Dihydro-7-methyl-9-oxo-3-acridinecarboxylic Acid, Methyl Ester

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6228DimethylformamideCatalyst

Procedure

A mixture of compound 138B (50 mg), MeOH (12 mL), Conc. H2SO4 (2 drops), and DMF (2 drops) was heated to reflux over 18 h. LC/MS indicated the reaction was complete. The reaction mixture was concentrated in vacuo to give a brown oil (47.5 mg). HPLC retention time: 3.05 min., condition: A. M+: 268.

Workup

  1. temperaturewas heated
  2. temperatureto reflux over 18 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-715694cf05ec42d8bb8b3d6821343aac
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

Loading…