Ethanol → ethyl quinoline-2-carboxylate

HRID 1110026Notes

Reaction equation

HRID 1110026 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[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH2:19][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7124Quinaldic Acid

Product 1

HCID 421739ethyl quinoline-2-carboxylate

Procedure

29.89 g of quinoline-2-carboxylic acid were heated under reflux for 51/2 hours in 450 ml of ethanol with the addition of 3.5 ml of sulfuric acid. The reaction mixture was worked up by evaporating it, taking up the residue in water and extracting the mixture with dichloromethane. The organic phase was washed with aqueous sodium bicarbonate solution and then with water until neutral, dried and evaporated. 32.23 g of crude ethyl quinoline-2-carboxylate were obtained as a green oil.

Workup

  1. customby evaporating it
  2. extractionextracting the mixture with dichloromethane
  3. washThe organic phase was washed with aqueous sodium bicarbonate solution
  4. dry with materialwith water until neutral, dried
  5. customevaporated

Sources & evidence

ORD record
ord-976e133b766b461e9cb7d0504ebe0de8
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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