Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 5-Bromo-2-fluoro-3-methylpyridine | HCID 12056902 | — |
| Reactant | 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide | HCID 54472560 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 54428942 | HCID 54428942 | 62.3% |
Reaction Steps
Sodium hydride (60%, 0.18 g, 4,5 mmol) was added to a solution of 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide (1.0 g, 4.5 mmol) in dry THF (25 mL) and stirred for 10 minutes at 25° C. under N2 atmosphere. The pyridine product of Example 1 (0.86 g, 4.5 mmol) was added to this reaction mixture and stirred for 16 hours. Water (20 mL) was added and the resulting mixture was extracted with ether (3×50 mL), dried (anhydrous Na2SO4), filtered and concentrated in vacuo to yield crude residue (1.5 g), which was then triturated with ether/pentane to give α-(methoxyimino)-N-methyl-2-[[[5-bromo-3-methyl-2-pyridinyl]oxy]methyl]-benzeneacetamide (1.1 g) as a white solid. M.P. 115-116° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05968875 |
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| Source dataset | uspto-grants-1999_10 |
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| ORD ID | ord-6f158ceb4b5b4723965e68f63ad13104 |
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| Source note | uspto-grants-1999_10 |
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