Acetic Acid → Methyl-2-oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylate

HRID 641133Notes

Reaction equation

HRID 641133 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]=[CH2:13])=[C:10]([C:14]([OH:16])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[N+](=[CH2:19])=[N-].C(O)(=O)C>CO.C(OCC)C>[CH3:19][O:15][C:14]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:1])[C:11]=1[CH:12]=[CH2:13])=[O:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 124162522-Oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylic acid

Product 1

HCID 12294102Methyl-2-oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4.4 g (20 mmol) 2-Oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylic acid 4 in 200 mL methanol was added etheral diazomethane at ambient temperature until the vigorous evolution of nitrogen subsided and the starting material was used up. Then 10 mL acetic acid were added, the mixture was diluted with 200 mL diethylether and washed with a solution of sodium bicarbonate (5%) and brine. The organic layer was separated, dried over sodium sulfate and filtered. After evaporation the crude product was purified by chromatography on silica gel eluting with toluene/ethyl acetate/methanol 4:1:1, to give 2.6 g of 5 as a pale yellow solid.

Workup

  1. washwashed with a solution of sodium bicarbonate (5%) and brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customAfter evaporation the crude product
  6. customwas purified by chromatography on silica gel eluting with toluene/ethyl acetate/methanol 4:1:1

Sources & evidence

ORD record
ord-252296e455384511b0f115e6e41e8d2f
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

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