Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium thiocyanate | HCID 516872 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 1-(2-Amino-3-methoxyphenyl)ethan-1-one | HCID 13691141 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86251909 | HCID 86251909 | 58% |
Reaction Steps
Under an atmosphere of nitrogen and at a temperature of 65° C., sodium borohydride (154 mg, 4 mmol) was added to a solution of 1-(2-amino-3-methoxy-phenyl)-ethanone (960 mg, 6 mmol) in ethanol (8 ml). After stirring at 65° C. overnight, water (5 ml), a solution of potassium thiocyanate (620 mg, 6 mmol) in water (3 ml), and a solution of conc. HCl (3 ml) in water (4 ml) were added subsequently. The mixture was then stirred for an additional 3 h at 65° C. Upon cooling, the solvent was evaporated and the residue was taken up in water/ethyl acetate. The organic phase was dried (Na2SO4), and the solvent was evaporated. Chromatography (silica gel, heptan/ethyl acetate=100/0-70/30) gave the title compound (700 mg, 58%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07790733B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-cb6a2b2fbc784f72bc06d1770b8b9ec0 |
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| Source note | uspto-grants-2010_09 |
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