HCID 178418361, compound → HCID 178517392, compound

HRID 2294201Notes

Reaction equation

HRID 2294201 reaction equation
[N:1]([CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([OH:15])[C:6]=1[C:16]([O-:18])=O)=[N+]=[N-].[H][H]>CN(C)C=O.[Pd]>[OH:15][C:7]1[C:6]2[C:16](=[O:18])[NH:1][CH2:4][C:5]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178514556HCID 178514556, compound

Product 1

HCID 178517392HCID 178517392, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

0.27 g (0.0010 mol) of 4-azidomethyl-2-hydroxy-quinoline-3-carboxylate was dissolved in 20 ml of hot dimethylformamide and treated with 14 mg of 10% Pd/C. A stream of hydrogen was introduced slowly during 11/2 hrs. The suspension was filtered under argon and the filtrate was partially concentrated under a high vacuum. The residue was treated with 25 ml of de-gassed ethanol, filtered off, dried in a vacuum and there were obtained ~60 mg (30%) of 4-hydroxy-2,3-dihydro-1 H-pyrrolo[3,4-c]quinolin-3-one as an air-sensitive, grey solid. The mother liquor was concentrated totally. The residue was dissolved in 75 ml of methanol and a stream of oxygen was conducted in slowly during 21/2 hrs. The mixture was filtered, concentrated, chromatographed over silica gel with ethyl acetate/methanol 9:1 as the eluent and the product was recrystallized from hot ethyl acetate. Yield: 0.033 g (15%) of 4-hydroxy-2,3-dihydro-1H-pyrrolo[3,4-c]-quinoline-1,3-dione as yellow crystals; m.p. 340°-350° C. (dec., subl.).

Workup

  1. filtrationThe suspension was filtered under argon
  2. concentrationthe filtrate was partially concentrated under a high vacuum
  3. additionThe residue was treated with 25 ml of de-gassed ethanol
  4. filtrationfiltered off
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-f3c3af838fbb45c592caa6f9fff95d10
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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