Water → HCID 19353251, compound

HRID 1250939Notes

Reaction equation

HRID 1250939 reaction equation
O1C2C=CC([CH:10]3[C:22]4[C:13](=[N:14][C:15]5[CH:16]=[C:17](C(OCC)=O)[C:18]6[O:25][CH:24](C(OCC)=O)[O:23][C:19]=6[C:20]=5[CH:21]=4)[C:12](=[O:36])[O:11]3)=CC=2OC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:43]>C1COCC1>[O:43]1[C:18]2[CH:17]=[CH:16][C:15]([C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]5[O:25][CH2:24][O:23][C:19]5=4)[N:14]=[C:13]4[C:12](=[O:36])[O:11][CH2:10][C:22]=34)=[CH:20][C:19]=2[O:23][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 131723099HCID 131723099, compound

Product 1

HCID 19353251HCID 19353251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl 9-(1,3-benzodioxole-5-yl)-1,3-dioxolo[4,5- f]furo[3,4-b]quinoline-7(9H)-one dicarboxylate (2.4 g) was added gradually to a suspension of LAH (lithium aluminium hydride (2.0 g) in THF (50 ml) at 0° C. The mixture was stirred at room temperature for one hour, followed by addition of water to stop the reaction. The resulting precipitate was filtered off through Celite®. The filtrate was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (100 ml) and, with addition of 10% Pd-C (2.5 g), stirred at room temperature overnight. The catalyst was filtered off, and the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform (300 ml), followed by addition of manganese dioxide (20 g). The mixture was stirred at room temperature for 3 hours. The manganese dioxide was filtered off through Celite®. The filtrate was concentrated under reduced pressure. The resulting crude crystals were washed with diisopropyl ether to yield the title compound (0.9 g). Some portions of the compound were recrystalized from THF to be used for elemental and instrumental analysis.

Workup

  1. customthe reaction
  2. filtrationThe resulting precipitate was filtered off through Celite®
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol (100 ml) and, with addition of 10% Pd-C (2.5 g)
  8. stirringstirred at room temperature overnight
  9. filtrationThe catalyst was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. dissolutionThe residue was dissolved in chloroform (300 ml)
  12. additionfollowed by addition of manganese dioxide (20 g)
  13. stirringThe mixture was stirred at room temperature for 3 hours
  14. filtrationThe manganese dioxide was filtered off through Celite®
  15. concentrationThe filtrate was concentrated under reduced pressure
  16. washThe resulting crude crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-f03bb0551237471ba31cde2f09dd57bc
Source dataset
uspto-grants-2002_01
Patent number
US06340704B1

Reaction notes

Loading…