3-Amino-5-chlorobenzoic acid

light yellow crystal powder

3-Chloro-5-nitro-benzoic acid (1.590g, 7. [9MMOL)] was stirred under a hydrogen atmosphere in ethanol (40mL) with raney-nickel, (aqueous suspension, -0. 4g) at room temperature and pressure for 18 hours. The reaction mixture was then filtered through celite and evaporated to give the title compound (1.300g, 96percent). [OH] NMR [(400MHZ, ] [CDCI3)] 6.86 (1H, s), 7.18 [(1H, ] s), 7.22 (1H, s). LC/MS t=2.30 mins [[MH-]] 170.Isopropanol (78 mL), Ammonium chloride (0.18 g) and reduced iron (1.07 g) were added to a mixed solution of water (20 mL)After stirring at 90 ° C. for 1 hour, 3-Chloro-5-nitrobenzoic acid (Compound 0004-1, 1.1 g) was slowly added and stirred at 90 ° C. for 3 hours.The reaction solution was cooled to room temperature, washed with methanol, and the filtrate was evaporated under reduced pressure to obtain a crude product. Purification by silica gel column chromatography (methanol-chloroform) gave 3-amino-5-chlorobenzoic acid (Compound 0004-2, 368 mg) as a light brown solid.Intermediate J7(P): 3-((4-((4-((ierf-Butoxycarbonyl)amino)naphthalen-1-yl)oxy) pyrimidin-2-yl)amino)-5-chlorobenzoic acid. Intermediate G2(P) To a solution of Intermediate G2(P) (1.01 g, 2.72 mmol) in anhydrous THF (15 mL) was added (Compound 0004-2, 130 mg)In tetrahydrofuran (3.8 mL)Triethylamine (0.32 mL) was added and the mixture was ice-cooled.Propionyl chloride (0.15 mL) was added, the temperature was raised to room temperature and stirred for 1 hour.A saturated aqueous solution of sodium bicarbonate was added to the reaction solution, and the mixture was stirred for 1 hour and then allowed to stand overnight. A 5.0 mol / L sodium hydroxide aqueous solution (0.6 mL) was added and the mixture was stirred for 1.5 hours, A 5.0 mol / L sodium hydroxide aqueous solution (1 mL) was further added, and the mixture was stirred for 30 minutes.6.0 mol / L hydrochloric acid (3 mL) was added, then ethyl acetate and water were added and the mixture was separated, The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product.Purification by silica gel column chromatography (methanol-chloroform) gave 3-chloro-5-propionamidobenzoic acid (Compound 0004-3, 92 mg).

Molecular Weight:171.58
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:171.0087061
Monoisotopic Mass:171.0087061
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes