Methanol → HCID 178518246, compound

HRID 2294203Notes

Reaction equation

HRID 2294203 reaction equation
[N:1]([CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([Cl:16])=[C:12]([Cl:15])[CH:13]=2)[N:8]=[C:7]([OH:17])[C:6]=1[C:18]([O:20]CC)=O)=[N+]=[N-].[H][H].C[OH:26]>CN(C)C=O.[Pd]>[Cl:16][C:11]1[C:12]([Cl:15])=[CH:13][C:14]2[C:5]3[C:4](=[O:26])[NH:1][C:18](=[O:20])[C:6]=3[C:7]([OH:17])=[N:8][C:9]=2[CH:10]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 178418361HCID 178418361, compoundHCID 178470061HCID 178470061, compound

Product 1

HCID 178518246HCID 178518246, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

1.0 g (0.003 mol) of ethyl 4-azidomethyl-6,7-dichloro-2-hydroxy-quinoline-3-carboxylate was dissolved in a mixture of 80 ml of methanol and 20 ml of dimethylformamide and treated with 50 mg of 10% Pd/C. A stream of hydrogen was conducted in slowly during 11/4 hrs. The suspension was suction filtered and the filter cake was suspended in dimethylformamide. The mixture was filtered, concentrated, the residue was suspended in methanol and suction filtered. The substance (0.31 g) was suspended in dimethylformamide and an oxygen stream was conducted in slowly during 2 hrs. The mixture was concentrated and the product was recrystallized from dimethylformamide/methanol. Yield: 0.27 g (20%) of 7,8-dichloro-4-hydroxy-2,3-dihydro-1H-pyrrolo[3,4-c]-quinoline-1,3-dione as yellow crystals; m.p. >350° C.

Workup

  1. custom4 hrs
  2. filtrationsuction filtered
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. filtrationsuction filtered
  6. customslowly during 2 hrs
  7. concentrationThe mixture was concentrated
  8. customthe product was recrystallized from dimethylformamide/methanol

Sources & evidence

ORD record
ord-c0f4095a18b44334b62790ecb0e245c3
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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