Water → ETHYL 2-(QUINOLIN-4-YL)ACETATE

HRID 1814285Notes

Reaction equation

HRID 1814285 reaction equation
[CH2:1]([O:3][C:4]([CH:6](C(OCC)=O)[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2].[Na+].[Cl-].O>CS(C)=O>[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 22504141HCID 22504141, compound

Product 1

HCID 3002912ETHYL 2-(QUINOLIN-4-YL)ACETATEYield 48%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

4-(Bis-ethoxycarbonyl methyl)-quinoline (5.05 g, 17.6 mmol), NaCl (2.06 g, 35.2 mmol), and H2O (0.63 mL, 35 mmol) were combined with DMSO (22 mL) in a round-bottom flask fitted with a reflux condenser. The heterogeneous mixture was stirred and heated to 160° C. for 90 minutes. TLC analysis (silca, 20% EtOAc-hexanes) indicated complete consumption of the starting material. The reaction was allowed to cool to room temperature and then was diluted with H2O. The dilution was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. Purification by gradient elution chromatography (SiO2, 20% EtOAc-hexanes to 30% EtOAc-hexanes) gave 4-(ethoxycarbonyl methyl)-quinoline (1.81 g, 8.40 mmol) in 48% yield. MS (APCI) m/z 216.1 (M+H). 1H NMR (300 MHz) CDCl3 δ 8.87 (d, J=4.4 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 8.00 (d, J=8.4 Hz, 1H), 7.73 (m, 1H), 7.60 (m, 1H), 7.34 (d, J=4.5 Hz, 1H), 4.17 (q, J=7.1 Hz, 2H), 4.07 (s, 2H), 1.23 (t, J=7.2 Hz, 3H).

Workup

  1. customfitted with a reflux condenser
  2. customconsumption of the starting material
  3. temperatureto cool to room temperature
  4. additionwas diluted with H2O
  5. extractionThe dilution was extracted three times with EtOAc
  6. washwashed with brine solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customPurification
  11. washby gradient elution chromatography (SiO2, 20% EtOAc-hexanes to 30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-af9d8c5a08ea46649dc4df37d261d6f5
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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