HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Methyl 4-(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzoate | HCID 68534814 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide | HCID 86087188 | 85% |
Reaction Steps
Treatment of methyl 4-(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzoate (102) (0.76 g, 3.09 mmol) with a mixture of N,O-dimethylhydroxylamine hydrochloride and nBuLi gave 0.72 g (85%) of the title compound (103) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.02 (d, J=6.6 Hz, 6H), 1.80-1.95 (m, 1H), 2.28 (d, J=6.6 Hz, 2H), 3.28 (br s, 3H), 3.59 (br s, 3H), 3.80 (s, 3H), 6.84 (dd, J1=8.6 Hz, J2=2.5 Hz, 1H), 6.94 (d, J=2.6 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H). LCMS (ESI): m/z 276 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-14add0c85932412ea9d51d57a948ea50 |
| Source note | uspto-grants-2010_01 |