Ethanol → Ethyl 3-quinolinepropionate

HRID 1248413Notes

Reaction equation

HRID 1248413 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:2]=1.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][C:13]([O:15][CH2:21][CH3:22])=[O:14])[CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 124157513-(Quinolin-3-yl)propanoic acid

Product 1

HCID 14338577Ethyl 3-quinolinepropionate

Procedure

A solution 3-(3-quinolinyl)propanoic acid (4.4 g) and concentrated sulphuric acid (2 ml) in absolute ethanol (50 ml) was refluxed for 5 h. then, evaporated to dryness. Aqueous sodium bicarbonate (8%, 50 ml) was added, the mixture extracted with ether (2×100 ml) and the ethereal extracts dried (Na2SO4). Evaporation of the ether and distillation of the residual oil (150°/0.06 mm) gave the title compound (4.3 g).

Workup

  1. customevaporated to dryness
  2. additionAqueous sodium bicarbonate (8%, 50 ml) was added
  3. extractionthe mixture extracted with ether (2×100 ml)
  4. dry with materialthe ethereal extracts dried (Na2SO4)
  5. customEvaporation of the ether and distillation of the residual oil (150°/0.06 mm)

Sources & evidence

ORD record
ord-846cb8daed294abdadac59dfaddd99b2
Source dataset
uspto-grants-1985_06
Patent number
US04524071

Reaction notes

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