HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → 2-Methoxy-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methyl 6-chloro-2-methoxy-4-methylnicotinate | HCID 57441127 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 2-Methoxy-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester | HCID 86664321 | 45% |
Reaction Steps
A solution of 5.0 g (21.8 mmol) 6-chloro-2-methoxy-4-methylpyridine-3-carboxylic acid methylester, 2.0 g (24.0 mmol) morpholine and 6.0 ml (43.5 mmol) NEt3 in NMP (21 ml) was heated at 90° C. for 2 d. After cooling to RT the mixture was partiotionated between EtOAc and a 1M aq. NaHCO3 sol. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 2.7 g (9.8 mmol, 45%) 2-methoxy-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09168259B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-bdef43dc9143456dbdca893e1d84c827 |
| Source note | uspto-grants-2015_10 |