No renderable structure data available
COCC1=[N+](C=C(C=C1)Br)[O-]Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-bromo-2-(methoxymethyl)-1-oxidopyridin-1-ium |
|---|---|
| IUPAC Name | — |
| CAS Number | 638219-87-1 |
| Database ID | 67299910 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-bromo-2-(methoxymethyl)-1-oxidopyridin-1-ium (CAS 638219-87-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 67299910
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8b1e3c7689a1451988603951cbf17a9cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-2-methoxymethyl-pyridine-1-oxide (5.0 g, 22.7 mmol), triethylamine (12.7 ml, 91 mmol) and trimethylsilyl cyanide (9.1 ml, 68.2 mmol) in acetonitrile (10 ml) was heated in a sealed tube to 120° C. for 18 hours. After completion of the reaction, water was added to the reaction mixture and acetonitrile was removed. The crude material was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 3.0 g (58%) of the title compound. was removed The crude material was extracted with ethyl acetate The combined organic layers were washed with water and brine dried filtered evaporated The crude product was purified by silica gel chromatography
Source ID: ord-c4152d288f934e238b87bab0de3af629Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5-bromo-2-hydroxymethyl-pyridine-1-oxide (6.43 g, 31.5 mmol) in THF (200 ml) was added sodium hydride (1.51 g, 63.1 mmol) at 0° C., and then the reaction mixture was stirred at ambient temperature for 1 h. After cooling to 0° C., methyl iodide (2.90 ml, 46.6 mmol) was added. The temperature was raised to ambient temperature and the reaction mixture was heated to 70° C. for 1 h. After cooling to 0° C. the reaction mixture was quenched with MeOH. The solvents were removed, and the crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 4.8 g (70%) of the title compound. After cooling to 0° C. The temperature was raised to ambient temperature the reaction mixture was heated to 70° C. for 1 h After cooling to 0° C. the reaction mixture was quenched with MeOH The solvents were removed the crude product was purified by silica gel chromatography
Source ID: ord-21f9bab9c34a466ea9601788f5ada127Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5-bromo-2-hydroxymethyl-pyridine-1-oxide (6.43 g, 31.5 mmol) in THF (200 ml) was added sodium hydride (1.51 g, 63.1 mmol) at 0° C., and then the reaction mixture was stirred at ambient temperature for 1 h. After cooling to 0° C., methyl iodide (2.90 ml, 46.6 mmol) was added. The temperature was raised to ambient temperature and the reaction mixture was heated to 70° C. for 1 h. After cooling to 0° C. the reaction mixture was quenched with MeOH. The solvents were removed, and the crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 4.8 g (70%) of the title compound. After cooling to 0° C. The temperature was raised to ambient temperature the reaction mixture was heated to 70° C. for 1 h After cooling to 0° C. the reaction mixture was quenched with MeOH The solvents were removed the crude product was purified by silica gel chromatography
Source ID: ord-21f9bab9c34a466ea9601788f5ada127Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8b1e3c7689a1451988603951cbf17a9cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-2-methoxymethyl-pyridine-1-oxide (5.0 g, 22.7 mmol), triethylamine (12.7 ml, 91 mmol) and trimethylsilyl cyanide (9.1 ml, 68.2 mmol) in acetonitrile (10 ml) was heated in a sealed tube to 120° C. for 18 hours. After completion of the reaction, water was added to the reaction mixture and acetonitrile was removed. The crude material was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 3.0 g (58%) of the title compound. was removed The crude material was extracted with ethyl acetate The combined organic layers were washed with water and brine dried filtered evaporated The crude product was purified by silica gel chromatography
Source ID: ord-f4e229691fa544a5ab67d8582dc3f899Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-2-methoxymethyl-pyridine-1-oxide (5.0 g, 22.7 mmol), triethylamine (12.7 ml, 91 mmol) and trimethylsilyl cyanide (9.1 ml, 68.2 mmol) in acetonitrile (10 ml) was heated in a sealed tube to 120° C. for 18 hours. After completion of the reaction, water was added to the reaction mixture and acetonitrile was removed. The crude material was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 3.0 g (58%) of the title compound. was removed The crude material was extracted with ethyl acetate The combined organic layers were washed with water and brine dried filtered evaporated The crude product was purified by silica gel chromatography
Source ID: ord-f4e229691fa544a5ab67d8582dc3f899Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5-bromo-2-hydroxymethyl-pyridine-1-oxide (6.43 g, 31.5 mmol) in THF (200 ml) was added sodium hydride (1.51 g, 63.1 mmol) at 0° C., and then the reaction mixture was stirred at ambient temperature for 1 h. After cooling to 0° C., methyl iodide (2.90 ml, 46.6 mmol) was added. The temperature was raised to ambient temperature and the reaction mixture was heated to 70° C. for 1 h. After cooling to 0° C. the reaction mixture was quenched with MeOH. The solvents were removed, and the crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 4.8 g (70%) of the title compound. After cooling to 0° C. The temperature was raised to ambient temperature the reaction mixture was heated to 70° C. for 1 h After cooling to 0° C. the reaction mixture was quenched with MeOH The solvents were removed the crude product was purified by silica gel chromatography
Source ID: ord-dff00ff4b725402f848db5435530ede9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-2-methoxymethyl-pyridine-1-oxide (5.0 g, 22.7 mmol), triethylamine (12.7 ml, 91 mmol) and trimethylsilyl cyanide (9.1 ml, 68.2 mmol) in acetonitrile (10 ml) was heated to 120° C. for 18 hours in a sealed tube. After completion of the reaction, water was added to the reaction mixture and acetonitrile was removed. The crude material was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 3.0 g (58%) of the title compound. was removed The crude material was extracted with ethyl acetate the combined organic layers were washed with water and brine dried filtered evaporated The crude product was purified by silica gel chromatography
Source ID: ord-9dac1766745542339ee633ea7bb533beConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5-bromo-2-hydroxymethyl-pyridine-1-oxide (6.43 g, 31.5 mmol) in THF (200 ml) was added sodium hydride (1.51 g, 63.1 mmol) at 0° C., and then the reaction mixture was stirred at ambient temperature for 1 h. After cooling to 0° C., MeI (2.90 ml, 46.6 mmol) was added. The temperature was raised to ambient temperature and the reaction mixture was heated to 70° C. for 1 h. After cooling to 0° C. the reaction mixture was quenched with MeOH. The solvents were removed, and the crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 4.8 g (70%) of the title compound. After cooling to 0° C. The temperature was raised to ambient temperature the reaction mixture was heated to 70° C. for 1 h After cooling to 0° C. the reaction mixture was quenched with MeOH The solvents were removed the crude product was purified by silica gel chromatography
Source ID: ord-19dad4eafa5a40cf856e264c5ae0af8eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-2-methoxymethyl-pyridine-1-oxide (5.0 g, 22.7 mmol), triethylamine (12.7 ml, 91 mmol) and trimethylsilyl cyanide (9.1 ml, 68.2 mmol) in acetonitrile (10 ml) was heated in a sealed tube to 120° C. for 18 hours. After completion of the reaction, water was added to the reaction mixture and acetonitrile was removed. The crude material was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 3.0 g (58%) of the title compound. was removed The crude material was extracted with ethyl acetate The combined organic layers were washed with water and brine dried filtered evaporated The crude product was purified by silica gel chromatography
Source ID: ord-c4152d288f934e238b87bab0de3af629Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 5-bromo-2-hydroxymethyl-pyridine-1-oxide (6.43 g, 31.5 mmol) in THF (200 ml) was added sodium hydride (1.51 g, 63.1 mmol) at 0° C., and then the reaction mixture was stirred at ambient temperature for 1 h. After cooling to 0° C., methyl iodide (2.90 ml, 46.6 mmol) was added. The temperature was raised to ambient temperature and the reaction mixture was heated to 70° C. for 1 h. After cooling to 0° C. the reaction mixture was quenched with MeOH. The solvents were removed, and the crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 4.8 g (70%) of the title compound. After cooling to 0° C. The temperature was raised to ambient temperature the reaction mixture was heated to 70° C. for 1 h After cooling to 0° C. the reaction mixture was quenched with MeOH The solvents were removed the crude product was purified by silica gel chromatography
Source ID: ord-21f9bab9c34a466ea9601788f5ada127PubChem References
These sources are listed in the compound's public database record.
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