HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → 2-Chloro-6,N,N-trimethyl-isonicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-6-methylpyridine-4-carboxylic acid | HCID 141209 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Chloro-6,N,N-trimethyl-isonicotinamide | HCID 56966855 | — |
Reaction Steps
To a solution of 2-Chloro-6-methyl-isonicotinic acid (1 g) in DMF (200 ml) at 25° C. was added DIPEA (2.9 mL) and TBTU (1.8 ml). After 5 min, dimethylamine (0.75 g) was added dropwise. This was stirred overnight. The reaction was added to water and extracted with EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash chromatography (9:1 to 2:8 gradient cyclohexane:EtOAc) afforded the title compound (320 mg). Rf=0.56 (1:1 cyclohexane:EtOAc)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08653075B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-70313f00a4a9493bb6a4f5a3de3d76a6 |
| Source note | uspto-grants-2014_02 |