Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tert-Butyl nitrite | HCID 10906 | — |
| Reactant | HCID 59238226 | HCID 59238226 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59238221 | HCID 59238221 | — |
Reaction Steps
Tert-butyl nitrite (1.1 mL) is added to a 60° C.-warm solution of CuCN (0.36 g) in DMSO (3 mL). Then, a solution of 4-bromo-2-(4-ethyl-benzyl)-5-methoxy-phenylamine (1.0 g) in DMSO is added dropwise and the resulting solution is stirred for 1 h at 60° C. After cooling to room temperature, the solution is acidified by the addition of 5 N aqueous hydrochloric acid. The resulting mixture is extracted with ethyl acetate and the combined extracts are dried (Na2SO4). After removal of the solvent, the residue is purified by chromatography on silica gel (cyclohexane/dichloromethane 3:1->1:3) to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07879806B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-bb8aa80268f8444b9b8e40949a7c6025 |
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| Source note | uspto-grants-2011_02 |
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