Ammonium cerium-nitrate → 6-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione

HRID 440351Notes

Reaction equation

HRID 440351 reaction equation
[N+]([O-])([O-])=[O:2].[NH4+].[Ce].[F:7][C:8]1[C:21]2[C:20]([OH:22])=[C:19]3[C:14]([CH:15]=[CH:16][N:17]=[CH:18]3)=[CH:13][C:12]=2[C:11]([O:23][CH3:24])=[CH:10][CH:9]=1>O.C(#N)C>[F:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[CH:18]=[N:17][CH:16]=[CH:15][C:14]=3[C:13](=[O:2])[C:12]=2[C:11]([O:23][CH3:24])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 57418452Ammonium cerium-nitrateHCID 1354566669-Fluoro-10-hydroxy-6-methoxybenzo[g]isoquinoline

Product 1

HCID 104913596-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dioneYield 37.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution of cerium ammonium nitrate (CAN; 13.70 g) in water (50 mL) is added during twenty minutes to a stirred suspension of 9-fluoro-10-hydroxy-6-methoxybenzo[g]isoquinoline (1.22 g) in acetonitrile (150 mL). At the end of the addition the obtained suspension is heated at 60° C. for two hours to give a clear, dark solution which is cooled to room temperature and diluted with water (100 mL). Following removal of acetonitrile by distillation at reduced pressure the aqueous phase is saturated with sodium chloride and extracted with methylene chloride (3×150 mL). The combined organic solutions are dried over anhydrous sodium sulphate and the solvent is removed at reduced pressure. The obtained residue is purified by silica-gel column chromatography (eluant: methylene chloride/ethyl acetate from 85/15 to 75/25 v/v) to give 9-fluoro-6-methoxybenzo[g]isoquinoline5,10-dione as a brown-yellow solid (0.48 g).

Workup

  1. additionAt the end of the addition the obtained suspension
  2. customto give a clear, dark solution which
  3. temperatureis cooled to room temperature
  4. customremoval of acetonitrile
  5. distillationby distillation at reduced pressure the aqueous phase
  6. extractionextracted with methylene chloride (3×150 mL)
  7. dry with materialThe combined organic solutions are dried over anhydrous sodium sulphate
  8. customthe solvent is removed at reduced pressure
  9. customThe obtained residue is purified by silica-gel column chromatography (eluant: methylene chloride/ethyl acetate from 85/15 to 75/25 v/v)

Sources & evidence

ORD record
ord-a191d52b3b4a41a1af9391e8d43b15b7
Source dataset
uspto-grants-1996_05
Patent number
US05519029

Reaction notes

Loading…