ethyl 2-ethoxy-2-iminoacetate;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An alternative route to this product comprises heating a mixture of ethyl 6,7-dimethoxy-2-aminoquinoline-3-carboxylate (1.38 g., 5.0 mM), ethyl 1-carbethoxyformimidate hydrochloride (1.82 g., 10 mM), triethylamine (5.1 g., 5.0 mM), ethanol (50 ml.) and N,N-dimethylformamide (20 ml.) on a steam bath for 17 hours. The reaction mixture is cooled and the solid which separates filtered off, triturated with hot chloroform and then recrystallized from chloroform to give 0.170 g. of product. M.P. 273°-274° C. (dec.). An alternative route to this product comprises heating The reaction mixture is cooled the solid which separates filtered off triturated with hot chloroform recrystallized from chloroform to give 0.170 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An alternative route to this product comprises heating a mixture of ethyl 6,7-dimethoxy-2-aminoquinoline-3-carboxylate (1.38 g., 5.0 mM), ethyl 1-carbethoxyformimidate hydrochloride (1.82 g., 10 mM), triethylamine (5.1 g., 5.0 mM), ethanol (50 ml.) and N,N-dimethylformamide (20 ml.) on a steam bath for 17 hours. The reaction mixture is cooled and the solid which separates filtered off, triturated with hot chloroform and then recrystallized from chloroform to give 0.170 g. of product. M.P. 273°-274° C. (dec.). An alternative route to this product comprises heating The reaction mixture is cooled the solid which separates filtered off triturated with hot chloroform recrystallized from chloroform to give 0.170 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An alternative route to this product comprises heating a mixture of ethyl 6,7-dimethoxy-2-aminoquinoline-3-carboxylate (1.38 g., 5.0 mM), ethyl 1-carbethoxyformimidate hydrochloride (1.82 g., 10 mM), triethylamine (5.1 g., 5.0 mM), ethanol (50 ml.) and N,N-dimethylformamide (20 ml.) on a steam bath for 17 hours. The reaction mixture is cooled and the solid which separates filtered off, triturated with hot chloroform and then recrystallized from chloroform to give 0.170 g. of product. M.P. 273°-274° C. (dec.) An alternative route to this product comprises heating The reaction mixture is cooled the solid which separates filtered off triturated with hot chloroform recrystallized from chloroform to give 0.170 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A hydrogen chloride gas was introduced into a diethyl ether solution of an equimolar mixture of ethyl cyanoformate and ethanol at 0° C. or lower, and a precipitated crystal was filtered out and washed with diethyl ether to obtain ethyl ethoxycarbonylformimidate hydrochloride [H5C2O2CC(OC2H5)=NH.HCl]. 5.4 g of this hydrochloride, 40 ml of acetic acid, 5.0 g of phenacylamine hydrochloride (the same as used in Synthesis Example 2) and 4.85 g of anhydrous sodium acetate were mixed and reacted with stirring at 90° to 100° C. for 4 hours. lower, and a precipitated crystal was filtered out washed with diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An alternative route to this product comprises heating a mixture of ethyl 6,7-dimethoxy-2-aminoquinoline-3-carboxylate (1.38 g., 5.0 mM), ethyl 1-carbethoxyformimidate hydrochloride (1.82 g., 10 mM), triethylamine (5.1 g., 5.0 mM), ethanol (50 ml.) and N,N-dimethylformamide (20 ml.) on a steam bath for 17 hours. The reaction mixture is cooled and the solid which separates filtered off, triturated with hot chloroform and then recrystallized from chloroform to give 0.170 g. of product. M.P. 273°-274° C. (dec.). An alternative route to this product comprises heating The reaction mixture is cooled the solid which separates filtered off triturated with hot chloroform recrystallized from chloroform to give 0.170 g