Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 10535454 | HCID 10535454 | — |
| Reactant | tetrahydrofuran N-methylpyrrolidinone | HCID 22156051 | — |
| Reactant | HCID 178455851 | HCID 178455851 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68902066 | HCID 68902066 | 88% |
Reaction Steps
A transparent red-colored THF/NMP(50 mL/5 mL) solution of 6-chloro-2-methoxy-4-methyl-nicotinonitrile (2.00 g, 11.0 mmol) and Fe (acac)3 (387 mg, 1.1 mmol) was slowly added with 11 mL of n-propylmagnesium bromide (2M solution in diethyl ether) and then stirred for about 20 minutes. The mixture was then added with 10 mL of 1M HCl solution 10 mL and diluted with 300 mL of ethylacetate. The resulting organic layer was washed with water and a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and then filtered. A silica gel column chromatography (10% EtOAc/Hexane) was performed on the residue obtained by concentrating the above filtrate under reduced pressure and obtained 2.23 g (88%) of 2-methoxy4-methyl-6-propyl-nicotinonitrile in colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07601736B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-a3973e16918049d3bbaebe4795a1b7f8 |
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| Source note | uspto-grants-2009_10 |
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