HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Methyl 2-(hex-1-yn-1-yl)benzoate | HCID 11333401 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | 2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide | HCID 10776773 | 77% |
Reaction Steps
Treatment of methyl 2-(1-hexyn-1-yl)benzoate (157) (2.29 g, 10.6 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 2.0 g (77%) of the title compound (158) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.92 (t, J=7.2 Hz, 3H), 1.40-1.60 (m, 4H), 2.39 (t, J=7.0 Hz, 2H), 3.32 (br s, 3H), 3.50 (br s, 3H), 7.26-7.35 (m, 3H), 7.37-7.45 (m, 1H). LCMS (APCI): m/z 246 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-83f311921b774dd98a4dd15c314d7d91 |
| Source note | uspto-grants-2010_01 |