Water → HCID 19353251, compound

HRID 378249Notes

Reaction equation

HRID 378249 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1C2C=CC([C:16]3(C(OCC)=O)[CH:25]=[C:24]4[C:19]([CH:20]=[CH:21][C:22]5[O:28][CH2:27][O:26][C:23]=54)=[N:18][CH:17]3[C:29]([O:31][CH2:32]C)=[O:30])=CC=2OC1.[OH2:39]>C1COCC1>[O:39]1[C:22]2[CH:21]=[CH:20][C:19]([C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]5[O:28][CH2:27][O:26][C:23]5=4)[N:18]=[C:17]4[C:29](=[O:30])[O:31][CH2:32][C:16]=34)=[CH:24][C:23]=2[O:26][CH2:27]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 70271692HCID 70271692, compound

Product 1

HCID 19353251HCID 19353251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of and lithium aluminum Hydride (LAH) (2.0 g) in THF (50 ml) was gradually added diethyl 8-(1,3-benzodioxol-5-yl)-1,3-dioxolo[4,5-f]quinoline-7,8-dicarboxylate (2.4 g) which was synthesized by the ordinally method described in E. A. Fehnel, Journal of organic Chemistry, vol.31, 2899-2092, 1966 or W. Ried, et al., Chemische Berichte, vol.85,204-216, at 0° C. The mixture was stirred for 1 hour at room temperature. To the reaction mixture was added water to stop the reaction, then the insoluble solid was filtered off with Celite. The filtrate was extracted with ethyl acetate and the extract was washed with water and dried with magnesium sulfate. The solvent was removed by distillation and the obtained residue was dissolved in ethanol (100 ml), and 10% Pd--C (2.5 g) was added thereto. The mixture was stirred overnight at room temperature. The catalyst was filtered off, and the solvent was removed by distillation. The obtained residue was dissolved in chloroform (300 ml) and manganese dioxide (20 g) was added thereto, then the mixture was stirred for 3 hours at room temperature. The manganese dioxide was filtered off with Celite and the filtrate was concentrated under reduced pressure. The obtained crude crystals were washed with diisopropyl ether and the entitled compound (0.9 g) was obtained. For elemental analysis, some of the entitle compound was recrystallized from THF.

Workup

  1. customwas synthesized by the ordinally method
  2. customat 0° C
  3. customthe reaction
  4. filtrationthe insoluble solid was filtered off with Celite
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was removed by distillation
  9. dissolutionthe obtained residue was dissolved in ethanol (100 ml)
  10. addition10% Pd--C (2.5 g) was added
  11. stirringThe mixture was stirred overnight at room temperature
  12. filtrationThe catalyst was filtered off
  13. customthe solvent was removed by distillation
  14. dissolutionThe obtained residue was dissolved in chloroform (300 ml)
  15. additionmanganese dioxide (20 g) was added
  16. stirringthe mixture was stirred for 3 hours at room temperature
  17. filtrationThe manganese dioxide was filtered off with Celite
  18. concentrationthe filtrate was concentrated under reduced pressure
  19. customThe obtained crude crystals
  20. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-43378b2f3bf0439f98d784e5175ced53
Source dataset
uspto-grants-2000_02
Patent number
US06030967

Reaction notes

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