Benzoic acid, 4-cyano-, hydrazide (9CI)

Part A. (g) Preparation of 4-cyano-benzoic acid hydrazide 9:To a solution of 4-cyano-benzoic acid methyl ester (1.0 g, 13 mmol) in 30 mL of MeOH was added 3 mL of ΗCompound 1 (3g, 18.6mmol) was dissolved in MeOH (15ml) and NHIntermediate 22b; 4-Cyanobenzohydrazide; To a 250 mL round bottom flask charged with ethyl 4-cyanobenzoate (16.85 g, 96.2 mmol) in 95percent ethanol (75 mL) was added hydrazine mono-hydrate (18.2 mL, 64percent solution, 240 mmol). This mixture was heated to reflux for a period of 4.5 h, then allowed to cool to room temperature over a 16 h period. The solvent was removed under reduced pressure and the yellow residue was taken up in ice-cold water (150 mL). The light yellow solid was filtered off and washed with additional cold water (50 mL). The solid was then dried under high vacuum to yield the title compound as a light yellow solid (13.98 g, 90percent). Synthesis of 3-[5-(4-Cyano-phenyl)-l, 3, 4-oxadiazol-2-ylmethyl]-N-((S)-6- morpholin-4-yl-4, 5, 6, 7-tetrahydro-benzothiazol-2-yl)-benzamide (Compound 40) Add hydrazine monohydrate (5.50 mL, 110 mmol) to a solution of methyl 4-cyanobenzoate (3.30 g, 20.5 mmol) in 20 mL of EtOH. Heat the mixture at 80 °C for 1 h resulting in a solution. Cool the mixture to room temperature, causing a solid to precipitate from solution. Collect the precipitate by filtration, wash with cold EtOH followed by diethyl ether to provide 1.90 g, 58percent yield of 4-cyano-benzoic acid hydrazide as a light yellow solid.

Molecular Weight:161.16
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:161.058911855
Monoisotopic Mass:161.058911855
Topological Polar Surface Area:78.9
Heavy Atom Count:12
Complexity:210
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes