Ethanol → ethyl quinoline-3-carboxylate

HRID 253113Notes

Reaction equation

HRID 253113 reaction equation
S(=O)(=O)(O)O.[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([C:16]([O-:18])=[O:17])[CH:7]=1.[K+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:26](O)[CH3:27]>>[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([C:16]([O:18][CH2:26][CH3:27])=[O:17])[CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 66844758HCID 66844758, compound

Product 1

HCID 282842ethyl quinoline-3-carboxylate

Conditions

Temperature
85 °C

Procedure

In a sealable tube, concentrated sulfuric acid (32 □L) was added to a solution of potassium quinoline-3-carboxylate in ethanol (1 mL). The flask was sealed and heated at 85° C. for 24 h. The mixture was cooled to ambient temperature, basified with 1 M sodium carbonate (10 mL), and the product was extracted with dichloromethane (3×15 mL). The organic fractions were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (10% to 20% EtOAc/hexane) afforded the title compound (292 mg, 1.45 mmol). MS m/z: 202 (M+1).

Workup

  1. customThe flask was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionthe product was extracted with dichloromethane (3×15 mL)
  4. dry with materialThe organic fractions were dried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the product by flash column chromatography (10% to 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-0d63f10c61594e5f86058856b88707e0
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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