N-ethylpropan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-ethylpropylamine (572 μL, 4.9 mmol) are added. The reaction stirred at room temperature 16 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+. The reaction is partitioned between ethyl acetate and water The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride dried (sodium sulfate) filtered concentrated under reduced pressure Purification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: According to the same manner as that described in Example 29, ethyl 2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate was reacted with N-ethyl-N-propylamine to give ethyl 2-(N-ethyl-N-propylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate. Colorless prisms, mp. 105°-106° C.

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

Procedure: According to the same manner as that described in Example 29, ethyl 2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate was reacted with N-ethyl-N-propylamine to give ethyl 2-(N-ethyl-N-propylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate. Colorless prisms, mp. 105°-106° C.

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

Procedure: To 100 mL of methylene chloride cooled to 0° C. is added 2-(trimethylsilyloxy)-1,3-butadiene (14.2 g, 0.1 mol), 8.5 g (0.1 mol) of N-ethyl-propanamine, and 14.2 g (0.1 mol) of borontrifluoride etherate. Monitor the reaction by thinlayer chromatography. Upon completion add 1N HCl until gas evolution ceases. Separate the aqueous layer and make it alkaline with 1N NaOH. Extract twice with 100 mL ether and dry over Na2SO4. Filter the drying agent and evaporated the solvent in vacuo to obtain the title compound. Monitor the reaction by thinlayer chromatography Separate the aqueous layer Extract twice with 100 mL ether dry over Na2SO4 Filter the drying agent evaporated the solvent in vacuo