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C) Preparation of p-cyano-dihydrocinnamic acid. By methods substantially equivalent to those described in Example 1-D, using 1.1 equivalent of LiOH.H2 O, 5.1 g (58%) of p-cyano-dihydrocinnamic acid were prepared from methyl p-cyano-dihydrocinnamate.
C) Preparation of p-cyano-dihydrocinnamic acid By methods substantially equivalent to those described in Example 1-D, using 1.1 equivalent of LiOH.H2 O, 5.1 g (58%) of p-cyano-dihydrocinnamic acid were prepared from methyl p-cyano-dihydrocinnamate.
C) Preparation of p-cyano-dihydrocinnamic acid By methods substantially equivalent to those described in Example 1-D, using 1.1 equivalent of LiOH.H2 O, 5.1 g (58%) of p-cyano-dihydrocinnamic acid were prepared from methyl p-cyano-dihydrocinnamate.
methyl 4-(2-methoxycarbonyl-ethyl)-iminobenzoate[ No CAS ]
[ 43038-36-4 ]
[ 75567-85-0 ]
[ 149899-18-3 ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; In water;
EXAMPLE 9 3-(4-Cyano-phenyl)-5-[4-(2-methoxycarbonyl-ethyl)-phenyl]-1,2,4-triazole 3.0 g of methyl 4-(2-methoxycarbonyl-ethyl)-iminobenzoate (prepared from 4-(2-methoxycarbonyl-ethyl)-benzonitrile and methanolic hydrochloric acid), 2.0 g of 4-cyano-benzohydrazide and 45 ml of pyridine are heated to 50 C. for 6 hours. The mixture is poured onto 250 ml of water, extracted with 150 ml of methylene chloride, the organic phase is washed with water and 2N hydrochloric acid, evaporated down, and the residue is separated, by chromatography on silica gel, into the components (eluant: methylene chloride/methanol=9:1). Yield: 1.0 g (22% of theory), Rf value: 0.68 (silica gel; methylene chloride/methanol=8:2) The following compound is obtained analogously:
With hydrogenchloride; sodium chloride; In tetrahydrofuran; water;
REFERENCE EXAMPLE 79 STR116 A solution of 1M superhydride/tetrahydrofuran (3.3 ml) in anhydrous tetrahydrofuran (5 ml) was cooled to -50° to -60° C. under an argon gas stream. Thereto was added dropwise a solution of 210 mg of methyl 3-(4-cyanophenyl)propionate synthesised from 4-cyanobenzaldehyde and methyl (triphenylphosphoranylidene)acetate by the procedure of Reference Examples 69 and 76) in 2 ml of tetrahydrofuran. The resultant mixture was stirred at that temperature for 10 minutes, then made acidic by addition of water and 1N hydrochloric acid in that order at the same temperature, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 120 mg of 3-(4-cyanophenyl)propanol. NMR (CDCl3) delta: 1.61~2.20 (3H), 2.60~3.06 (2H), 3.68 (2H, t, J=6 Hz), 7.10~7.75 (4H)
Preparation 37 Methyl 3-(4-cyanophenyl)propanoate To a solultion of Preparation 39 (680mg, 3.88mmol) in methanol (8mL) and dichloromethane (8mL) at 0C was added trimethylsilyldiazomethane (2M in hexane, 3.9mL) until a yellow color persisted. The reaction mixture was stirred at room temperature for 1h and was concentrated to dryness to give the title compound, which was used without further purification (87% yield). LRMS: no signal Retention time: 5.42min (Method B) 1H NMR (200 MHz, CHLOROFORM-D) delta ppm 2.7 (t, J=7.4 Hz, 2 H) 3.0 (t, J=7.4 Hz, 2 H) 3.7 (s, 3 H) 7.3 (d, J=8.4 Hz, 2 H) 7.6 (d, J=8.4 Hz, 2 H)
<strong>[42287-94-5]4-cyanobenzenepropionic acid</strong> (1g, 5.7 mmol) and methanol (10 mL) were added to a 25 mL single-mouth bottle, thionyl chloride (0.5 mL) was added dropwise at room temperature, and the mixture reacted at room temperature for 3 hours while stirring. After the reaction, the mixture was concentrated in vacuo to remove the solvent under a reduced pressure, and the resulting crude product was dissolved in ethyl acetate (20 mL), and washed with saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentrated in vacuo to give the product (colorless oil, 960 mg). 1H NMR (400 MHz, CDCl3) delta 7.57 (d, J= 8.2 Hz, 2H), 7.30 (d, J= 8.1 Hz, 2H), 3.66 (s, 3H), 3.00 (t, J= 7.6 Hz, 2H), 2.64(t, J= 7.6 Hz, 2H). MS (ESI) m/z: 190.1 (MH+).