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[ CAS No. 28232-53-3 ]

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2D
Chemical Structure| 28232-53-3
Chemical Structure| 28232-53-3
Structure of 28232-53-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 28232-53-3 ]

CAS No. :28232-53-3MDL No. :MFCD05855249
Formula : C11H8N2O3 Boiling Point : 345°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :216.19Pubchem ID :-
Synonyms :

Computed Properties of [ 28232-53-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 28232-53-3 ]

Signal Word:Class:N/A
Precautionary Statements:UN#:N/A
Hazard Statements:Packing Group:N/A

Application In Synthesis of [ 28232-53-3 ]

  • Upstream synthesis route of [ 28232-53-3 ]
  • Downstream synthetic route of [ 28232-53-3 ]

[ 28232-53-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 28232-53-3 ]
  • [ 80650-45-9 ]
YieldReaction ConditionsOperation in experiment
99% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Synthesis of compound 34-2 (0476) To the solution of 34-1 (2.0 g, 9.259 mmol) in MeOH (20 mL) was added 10percent Pd/C (0.2 g) purged with N2. Then H2 was added to remove N2. The mixture was stirred at room temperature overnight. After filtrated, the filtrate was concentrated to dryness affording 34-2 (1.7 g, 99percent) as brown solid.
98% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Step 4. 4-(Pyridin-3-yloxy) aniline. 3-(4-nitrophenoxy)pyridine (10.2 g, 47.18 mmol) was dissolved in 100 mL MeOH, followed by addition of Pd/C powder (10percentwt, 1.1 g). The reaction mixture was stirred at r.t. under H2 atmosphere overnight and filtered through Celite. The filtrate was concentrated to afford 4-(pyridin-3-yloxy)aniline (17.45 g, 98percent yield) as grey solid. LC-MS: m/z: 187 (M+H)+.
95% With hydrogen In tetrahydrofuran; methanol at 20℃; b) Compound 5 was hydrogenated at room temperature using PD/C in MEOH/THF. The reaction solution was filtered through kieselguhr and rinsed with MEOH, and the filtrate was subsequently evaporated. The residue was digested with diethyl ether, filtered off with suction, rinsed with diethyl ether and dried overnight at 40'C under reduced pressure. Yield : 37. 14 G (95percent) OF 6, PALE-BROWN CRYSTALS
95% With hydrogen In tetrahydrofuran; methanol at 20℃; The thus obtained nitro comound was hydrogenated at room temperature using Pd/C in MeOH/THF. The reaction solution was filtered through kieselguhr and rinsed with MeOH, and the filtrate was subsequently evaporated. The residue was digested with diethyl ether, filtered off with suction, rinsed with diethyl, ether and dried overnight at 40°C under reduced pressure. Yield : 37.14 g (95percent) of 5b, pale-brown crystals
95% With hydrogen In tetrahydrofuran; methanol at 20℃; Compound 5 is hydrogenated with Pd/C in [METHANOL/TETRAHYDROFURANE] at room temperature. The reaction mixture is filtered over kieselguhr, the residue washed with methanol and the filtrate evaporated. The residue is digested with diethyl ether, filtered by suction, washed with diethyl ether and dried in vacuum at 40 [°C] overnight to yield 37.14 g (95 percent) light brownish crystals of 6.
95% With hydrogen In tetrahydrofuran; methanol at 20℃; b) Compound 5 is hydrogenated at room temperature using Pd/C in MeOH/THF. The reaction solution is filtered through kieselguhr and rinsed with MeOH, and the filtrate is subsequently evaporated. The residue is digested with diethyl ether, filtered off with suction, rinsed with diethyl ether and dried overnight at 40°C under reduced pressure. Yield : 37.14 g (95percent) of 6, pale-brown crystals
95% With hydrogen In ethyl acetate for 3.5 h; A solution of 3- (4-nitrophenoxy)pyridine g, 23.13 mmol) in EtOAc (100 mL) in a 250 ml Parr bottle was purged with nitrogen. To this solution was added EtOAc-moistened 10percent Pd/C catalyst (500 mg, 10percent by weight). The reaction flask was placed in a Parr hygrogenation apparatus, purged with nitrogen (5x), evacuated, and then pressurized to 40 psi with hydrogen and shaken for 3.5 h. The reaction mixture was then purged with nitrogen, and filtered through a pad of Celite , rinsing with ethyl acetate (3x) and ethanol (3x). The filtrate was evaporated at reduced pressure to give a brown crystalline residue. The residue was stirred in diethyl ether at room temperature for 16 h and then filtered to provide 4.11 g (95percent) of the desired product as light brown crystals. (at)H-NMR (DMSO-d6) No. 8.21 (m, 2H), 7.30 (ddd, J = 8.4,4.6, 0.7 Hz, 1 H), 7.18 (ddd, J = 8.4, 2.9, 1.4 Hz, 1 H), 6.79 (d, J = 8.8 Hz, 2H), 6.58 (d, J = 9.0 Hz, 2H), 5.05 (br s, 2H) ; MS LC-MS [M+H]+ = 187, RT = 1.03 min.
36% With iron; ammonium chloride In tetrahydrofuran; methanol; water at 80℃; for 3 h; 4-(Pyridin-3-yl)oxy-l -nitrobenzene prepared in Step A was dissolved in the mixture of water (100 mL), tetrahydrofuran (100 mL) and methanol (100 mL). Iron powder (103 g, 1.84 mol) and ammonium chloride (99 g, 1.84 mol) were added thereto, and the mixture was stirred for 3 h at 80 °C using a mechanical stirrer. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with methanol, and concentrated under reduced pressure. The solid thus obtained was filtered, washed with ether, and dried to give the title compound (17 g, Yield 36percent). Mass[M+H] : 186 (M+l)
36% With iron; ammonium chloride In tetrahydrofuran; methanol at 80℃; for 3 h; The compound thus obtained was dissolved using water (100ml), tetrahydrofuran (100ml) and methanol (100ml). Iron powder (103g, 1.84 mol) and ammonium chloride (99g, 1.84 mol) were added thereto, and the mixture was stirred using a mechanical stirrer for 3 h at 80 "C . After completion of the reaction, the reaction solution was filtered through a celite, washed with methanol, and concentrated.The resulting solid was filtered, washed with ether, and dried to give 4-(pyridin-3- yloxy)-phenylamine ( 17g, Yield 36percent).
36% With water; iron; ammonium chloride In tetrahydrofuran; methanol at 80℃; for 3 h; 4-(Pyridin-3-yl)oxy-1-nitrobenzene prepared in Step A was dissolved in the mixture of water (100 mL), tetrahydrofuran (100 mL) and methanol (100 mL). Iron powder (103 g, 1.84 mol) and ammonium chloride (99 g, 1.84 mol) were added thereto, and the mixture was stirred for 3 h at 80° C. using a mechanical stirrer. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with methanol, and concentrated under reduced pressure. The solid thus obtained was filtered, washed with ether, and dried to give the title compound (17 g, Yield 36percent).

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