Methanol → 6-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione

HRID 1636324Notes

Reaction equation

HRID 1636324 reaction equation
[CH3:1][O-:2].[Na+].CO.[Na].F[C:8]1[C:13]2[C:14](=[O:23])[C:15]3[CH:16]=[CH:17][N:18]=[CH:19][C:20]=3[C:21](=[O:22])[C:12]=2[C:11]([F:24])=[CH:10][CH:9]=1>C1COCC1.C(Cl)Cl>[F:24][C:11]1[C:12]2[C:21](=[O:22])[C:20]3[CH:19]=[N:18][CH:17]=[CH:16][C:15]=3[C:14](=[O:23])[C:13]=2[C:8]([O:2][CH3:1])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 101059046,9-Difluorobenzo[g]isoquinoline-5,10-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 104913596-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium methoxide, freshly prepared under nitrogen atmosphere from anhydrous methanol (97.6 ml) and sodium (2.024 g), is dropped in a time of 2 hours and 35 minutes into a solution of 6,9-difluorobenzo[g]isoquinolin-5,10-dione (19.615 g, preparation 3) in anhydrous THF (883 ml), under stirring and at room temperature. At the end of the addition, the reaction mixture is concentrated to half the starting volume, then is kept at 18° C. for 30 minutes. The separated solid is filtered and washed with 100 ml of THF, then it is suspended in water (80 ml), left overnight under stirring and filtered again to give 9.3 g of crude product, which is suspended in methylene chloride (45 ml) and refluxed for 30 minutes. After cooling at room temperature, the product is filtered and the separated solid is washed with methylene chloride (5×3 ml), then dried under vacuum at 40° C., to obtain 8.65 g of pure product, m.p. 248-250° C.

Workup

  1. additionAt the end of the addition
  2. concentrationthe reaction mixture is concentrated to half the starting volume
  3. filtrationThe separated solid is filtered
  4. washwashed with 100 ml of THF
  5. waitleft overnight
  6. stirringunder stirring
  7. filtrationfiltered again
  8. customto give 9.3 g of crude product, which
  9. temperaturerefluxed for 30 minutes
  10. temperatureAfter cooling at room temperature
  11. filtrationthe product is filtered
  12. washthe separated solid is washed with methylene chloride (5×3 ml)
  13. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-9f9e0d67746c48bcbd60d6c70777d1c2
Source dataset
uspto-grants-2000_03
Patent number
US06034092

Reaction notes

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