HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 3-Bromo-6-chloro-N-methoxy-N-methylpicolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-Bromo-6-chloropyridine-2-carboxylic acid | HCID 26966732 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-Bromo-6-chloro-N-methoxy-N-methylpicolinamide | HCID 86666725 | — |
Reaction Steps
To a solution of 3-bromo-6-chloropicolinic acid (4.516 g, 19.10 mmol), N,O-dimethylhydroxylamine hydrochloride (3.73 g, 38.2 mmol), pyridine (4.63 mL, 57.3 mmol) in CH2Cl2 (40 mL) at 0° C. was added —N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (4.39 g, 22.92 mmol). After 1 h at 0° C., a saturated aqueous solution of ammonium chloride was added and the product was extracted with MTBE/EtOAc (4:1) (repeated 4 times). The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The product was carried out without purification in the next step. LC/MS m/z 281 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08796261B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-c16c1942239a4e66ae169960c651d2a5 |
| Source note | uspto-grants-2014_08 |