Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | 1-Naphthaleneacetonitrile | HCID 8596 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 12218643 | HCID 12218643 | — |
Reaction Steps
A solution of 16.7 g (100 mmol) of 1-naphthylacetonitrile in 200 m of DMF and 15 ml (240 mmol) of methyl iodide is mixed at 0° C. with 10.4 g (260 mmol) of sodium hydride (addition within 2.5 hours). The batch is stirred for 3 hours at 0° C. and for 18 hours at 25° C. It is mixed with ice and ethyl acetate. The organic phase is acidified with 10% H2SO4, washed three times with water, dried (NaSO4) and concentrated by evaporation in a vacuum. A large-scale purification is carried out by bulb tube distillation (boiling range 60–130° C.) in an oil pump vacuum; yield: 18.8 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07166592B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-8e794ce147f44760b7f38edc223b5da7 |
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| Source note | uspto-grants-2007_01 |
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