Water → HCID 68874499, compound

Participants

Reaction Steps

Ethyl N-(3-nitroquinolin-4-yl)-β-alaninate (62.0 g, 214 mmol, prepared as described in Part A of Example 22) was treated with sodium hydrosulfite (130.59 g, 750.04 mmol), potassium carbonate (117 g, 847 mmol), and ethyl viologen dibromide (0.802 g, 2.14 mmol) according to a modification of the method described in Part A of Example 8. After the reaction was stirred overnight, additional water (100 mL), dichloromethane (100 mL) and sodium hydrosulfite (20.0 g, 11.5 mmol) were added, and the reaction was stirred for three additional hours. The organic layer was separated; washed sequentially with water, saturated aqueous sodium bicarbonate, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide 40.2 g of ethyl N-(3-aminoquinolin-4-yl)-β-alaninate.

Provenance & Evidence