Triethylamine → ethyl N-(((5-nitro-8-quinolinyl)oxy)carbonyl)glycinate

Reaction equation

[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].[N:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]=[O:17].C(N(CC)CC)C>C(C(C)=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][C:16]([NH:15][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:17])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2]

Participants

Procedure

5-Nitro-8hydroxyquinoline (19.0 g) was added to a solution containing 13.6 g of ethyl isocyanatoacetate in 250 ml of methyl ethyl ketone. This mixture was then stirred at room temperature while triethylamine (1.0 g) was added. Stirring was continued at ambient temperature for about 30 minutes when a crystalline mass precipitated. This crystalline solid was collected by filtration, washed with carbon tetrachloride and subsequently dried leaving the desired ethyl N-(((5-nitro-8-quinolinyl)oxy)carbonyl)glycinate as cream colored crystals, m.p. 121°-122° C.