Among the newer generation diuretics is bumetanide,

Chapter 23, Problem 23.7

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Among the newer generation diuretics is bumetanide, prescribed under several trade names, including Bumex and Fordiuran. Following is an outline of a synthesis of this drug. ? OO NO2 COOH 4-Chloro-3-nitrobenzoic acid Cl NO2 COOH Cl S 9ONa1 H2N ? OO NO2 COOH 9O S H2N O Bumetanide O N H COOH 9O S H2N 1 2 3 (a) Propose a synthesis of 4-chloro-3-nitrobenzoic acid from toluene. (b) Propose reagents for Step (1). (Hint: It requires more than one reagent.) (c) Propose a mechanism for reaction (2). (d) Propose reagents for Step (3). (Hint: It too requires more than one reagent.) (e) Is bumetanide chiral? If so, which of the possible stereoisomers are formed in this synthesis?

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