Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | 6-Azidomethylnicotinonitrile | HCID 18506740 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178514553 | HCID 178514553 | 100% |
Reaction Steps
To a solution of the azide of Example 51 (11-3) (6.46 g, 40.6 mmol) in methanol (100 ml) was added hydroxylamine hydrochloride (3.95 g, 56.84 mmol), followed by triethylamine (9.6 ml). The solution was heated to 65° C. for four hours. The solvent was removed under reduced pressure and the remaining residue was extracted with ethylacetate (300 ml) and water (100 ml). The water layer was re-extracted with ethylacetate (2×200 ml). The combined organic extracts were washed with brine (2×100 ml), dried over MgSO4 and evaporated to yield the title product (11-4) (7.8 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06586405B2 |
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| Source dataset | uspto-grants-2003_07 |
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| ORD ID | ord-5bd53f449c444882b95df0f337f1f7a1 |
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| Source note | uspto-grants-2003_07 |
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