Ethanol → Ethyl 3-quinolinepropionate
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:12][C:13]([O-:15])=[O:14])[CH:2]=1.[CH2:16](O)[CH3:17]>[Pd]>[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][CH2:16][CH3:17])=[O:14])[CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-quinolineacrylate (51.68 g) was dissolved in ethanol (170 ml) and hydrogenated at 37° and a pressure of 50 psi using 10% Palladium on charcoal to give ethyl 3-quinolinepropionate. p (iii) Ethyl 3-quinolinepropionate (47.99 g) and ethyl formate (16.3 g) were added over a period of 3 hours to a stirred mixture of sodium wire (4.8 g) and dry ether (150 ml) cooled by an ice-bath. The mixture was stirred for 20 hours at room temperature, evaporated to dryness and the residue was treated with thiourea (15.9 g) and ethanol (130 ml) and refluxed for 7 hours. The mixture was evaporated to dryness and the residue was dissolved in water and acetic acid added to pH 4. The mixture was filtered to give 5-(3-quinolinemethyl)-2-thiouracil, m.p. 281°-6° (decomp.) (ex. acetic acid-water).