Ethanol → 3,4-Dihydroxy-1-methylquinolin-2(1H)-one

HRID 1612761Notes

Reaction equation

HRID 1612761 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4](=NO)[C:3]1=[O:15].[H][H].C([OH:20])C>[Pd].Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([OH:20])[C:3]1=[O:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 178418361HCID 178418361, compoundHCID 178481576HCID 178481576, compound2×

Product 1

HCID 546957683,4-Dihydroxy-1-methylquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 1-methyl-3-oximino-quinolin-2,4(1H)-dione (1.7 gm, Formula 1.02, Example 1) and 10% palladium on charcoal (0.5 gm) in a mixture of ethanol (90 ml) and 2N hydrochloric acid (40 ml) was hydrogenated at atmospheric conditions. After 2.5 hrs no further uptake of hydrogen (510 ml) was observed. The reaction mixture was filtered and the solid cake was extracted with hot glacial acetic acid (2×100 ml). The combined filtrates were evaporated under reduced pressure and the produce was crystallized from acetic acid/water to give the title compound (1.6 gm). That the expected product was obtained was confirmed by the spectral data: MS (FAB): m/e 192 (M.+ +1); NMR (DMSO): δ3.66 (s, 3H, CH3 --N), 8.79 (s, 1H, OH), 10.16 (s, 1H, OH) ppm.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionthe solid cake was extracted with hot glacial acetic acid (2×100 ml)
  3. customThe combined filtrates were evaporated under reduced pressure
  4. customthe produce was crystallized from acetic acid/water

Sources & evidence

ORD record
ord-bc801b02f3114cc9a73aa81d76976dc7
Source dataset
uspto-grants-1993_03
Patent number
US05190956

Reaction notes

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