Sodium Hydroxide → 2-Ethylthiazolo[4,5-c]quinoline

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:13](OC(=O)CC)(=O)[CH2:14][CH3:15].[OH-].[Na+]>Cl>[CH2:14]([C:15]1[S:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:13]

Participants

Procedure

A mixture of 17.62 g (0.1 mole) of 3-amino-4-mercapto-quinoline and 85 ml of propionic anhydride is first slowly heated to boiling and then refluxed for one hour and a half. The reaction mixture is added dropwise to 800 ml of 1% aqueous hydrochloric acid under vigorous stirring. The homogenous solution is made alkaline to pH 10 by adding sodium hydroxide solution and extracted three times with 200 ml of benzene each. The benzene solution is evaporated. Thus 19.26 g of 2-ethylthiazolo[4,5-c]quinoline are obtained, yield 90%, m.p.: 48°-49° C.