Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | 5-Isobutyl-4-methyl-pyridine-2-carbonitrile | HCID 68628343 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178426677 | HCID 178426677 | 123% |
Reaction Steps
To a solution of 5-isobutyl-4-methyl-pyridine-2-carbonitrile (106 mg, 608 μmol) in methanol (3 mL), triethylamine (123 mg, 1.22 mmol) and hydroxylamine hydrochloride (63 mg, 913 μmol) is added. The mixture is stirred at 75° C. for 18 h before it is concentrated. The residue is dissolved in aq. NaHCO3 (pH 7-8) and extracted with DCM (6×50 mL). The org. extracts are combined, dried over MgSO4, filtered, concentrated and dried to give the title compound (155 mg) as a white solid; LC-MS: tR=0.67 min, [M+1]+=208.01; 1H NMR (CD3OD): δ0.97 (d, J=6.8 Hz, 6H), 1.84-1.96 (m, 1H), 2.37 (s, 3H), 2.58 (d, J=7.3 Hz, 2H), 7.67 (s, 1H), 8.26 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08575200B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-6c53aefacff8406080cc3eea8458ab2e |
|---|
| Source note | uspto-grants-2013_11 |
|---|