Structure of 13024-16-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 13024-16-3 |
Formula : | C13H13NO |
M.W : | 199.25 |
SMILES Code : | NC1=CC=C(OC2=CC=CC=C2)C=C1C |
MDL No. : | MFCD08688317 |
Boiling Point : | No data available |
InChI Key : | LOXZCYZBCSAIIF-UHFFFAOYSA-N |
Pubchem ID : | 20406519 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tin(ll) chloride; In methanol; water; at 20℃; for 12h; | General procedure: 4-(2-Fluoro-phenoxy)-2-methyl-1-nitro-benzene was reduced using the conditions outlined inGeneral Procedure B to give 4-(2-fluoro-phenoxy)-2-methyl-phenylamine. General Procedure B: Reduction of the Nitro Group A solution of tin(II) chloride (3 equivalents) in hydrochloric acid was added to a stuffed solution of the nitro compound in MeOH. The mixture was stirred at room temperature for 12 h, and then evaporated under reduced pressure. The residue was made alkaline by adding 2 N NaOH solution. The mixture was extracted with EtOAc. The organic extract was dried (Na2SO4),filtered, and evaporated. The residue was purified by chromatography on silica gel to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With palladium on activated charcoal; hydrogen; In methanol; under 760.051 Torr; for 18h; | A solution of 2-methyl-l-nitro-4-phenoxybenzene (63 g, 275 mmol) in MeOH (500 mL) was added Pd/C (10 g). The mixture was stirred under H2 atmosphere (1 atm) for 18 h. The mixture was filtered and concentrated to afford 2-methyl-4-phenoxyaniline (51 g, 93%) as a brown solid which was used in the next step without purification. |
90% | With iron; ammonium chloride; In ethanol; water; for 2h;Reflux; Inert atmosphere; | To a solution of 2-methyl-l-nitro-4-phenoxy benzene (100 g, 436 mmol) in EtOH/H20 (3: 1 ratio, 2000 mL) were sequentially added NH4C1 (117 g, 2180 mmol) and Fe (97 g, 1700 mmol). The reaction mixture was heated to reflux for 2 h, then the reaction was cooled to 25 C and concentrated to dryness. To the residue was added water and EtOAc and the organic layer was separated, washed with saturated NaHC03 and saturated brine, dried (MgS04), filtered, and concentrated to dryness to yield the title Compound (82 g, 90% yield). |
90% | With iron; ammonium chloride; In ethanol; water; for 2h;Reflux; | To a solution of 2-methyl-1-nitro-4-phenoxy benzene (100 g, 436 mmol) in EtOH/H20 (3: 1 ratio, 2000 mL) were sequentially added NH4ci (117 g, 2180 mmol) and Fe (97 g, 1700 mmol). The reaction mixture was heated to reflux for 2 h, then the reaction was cooled to 25 C and concentrated to dryness. To the residue was added water and EtOAc and the organic layer was separated, washed with saturated NaHCC and saturated brine, dried over anhydrous MgSC>4, filtered, and concentrated to dryness to yield the title compound (82 g, 90% yield). |
90% | With iron; ammonium chloride; In ethanol; water; for 2h;Reflux; | To a solution of 2-methyl-1-nitro-4-phenoxybenzene (100 g, 436 mmol) in EtOH/H20 (3:1 ratio, 2000 mL) were sequentially added NH4C1 (117 g, 2180 mmol) and Fe (97 g, 1700 mmol). The reaction mixture was heated to reflux for 2 h, then the reaction was cooled to 25 C and concentrated to dryness. To the residue was added water and EtOAc and the organic layer was separated, washed with saturated NaHCO3 and saturated brine,dried (Mg504), filtered, and concentrated to dryness to yield the title compound (82 g, 90% |
90% | With iron; ammonium chloride; In ethanol; water; for 2h;Reflux; | To a solution of 2-methyl-1-nitro-4-phenoxybenzene (100 g, 436 mmol) in EtOH/H 2O (3: 1 ratio, 2000 mL) were sequentially added NH 4Cl (117 g, 2180 mmol) and Fe (97 g, 1700 mmol). The reaction mixture was heated to reflux for 2 h, then the reaction was cooled to 25 and concentrated to dryness. To the residue was added water and EtOAc and the organic layer was separated, washed with saturated NaHCO 3 and saturated brine, dried over anhydrous MgSO 4, filtered, and concentrated to dryness to yield the title compound (82 g, 90%yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | A suspension of <strong>[13024-16-3]2-methyl-4-phenoxyaniline</strong> (19 g, 95.5 mmol) in water (375 mL) was added HBr (150 mL, 40%) at 0C. After 30 min, NaN02 (6.9 g, 100 mmol) in water (75 mL) was added at 0 C. After 30 min, the mixture was added to a pre-heated suspension of CuBr (14.3 g, 100 mmol) in water (375 mL) at 65 C. The mixture was stirred at 65 C for 30 min, cooled, and extracted with petroleum ether. The combined organic layer was washed with water and dried over Na2S04. Purification by silica gel column chromatography afforded 1- bromo-2-methyl-4-phenoxybenzene (15 g, 60%) as a yellow oil. |
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