Water → 3-(2-Quinolinyl)-2-propenoic acid

HRID 1993779Notes

Reaction equation

HRID 1993779 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]([O:15]C)=[O:14].O.[OH-].[Na+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 6479253Methyl (E)-3-(2-quinolinyl)-2-propenoate

Product 1

HCID 7129193-(2-Quinolinyl)-2-propenoic acidYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (E)-3-(2-quinolinyl)-2-propenoate (2) (1.07 g, 5.02 mmol) in methanol (24 ml), a water solution of 1N NaOH (16 ml, 16.0 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. The mixture was supplemented with water (40 ml) and washed with ethyl acetate (40 ml). The aqueous layer was separated and the pH of the medium was brought to 5. The mixture was extracted with ethyl acetate (3×40 ml) and the combined extracts were dried (Na2SO4). The solvent was evaporated and the residue was dried in vacuum to give the title compound (0.49 g, 49%) as viscous oil. 1H NMR (DMSO-d6, HMDSO), δ: 7.02 (1H, d, J=15.7 Hz); 7.52-8.15 (5H, m); 7.75 (1H, d, J=15.7 Hz); 8.42 (1H, d, J=9.0 Hz); 12.69 (1H, br s).

Workup

  1. washwashed with ethyl acetate (40 ml)
  2. customThe aqueous layer was separated
  3. extractionThe mixture was extracted with ethyl acetate (3×40 ml)
  4. dry with materialthe combined extracts were dried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was dried in vacuum

Sources & evidence

ORD record
ord-b5bf06bde09842d1a0a91de18fbe8eb6
Source dataset
uspto-grants-2010_01
Patent number
US07652036B2

Reaction notes

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