HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4,6-Dichloronicotinic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ethyl 4,6-dichloropyridine-3-carboxylate | HCID 600045 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4,6-Dichloronicotinic acid | HCID 817158 | 96% |
Reaction Steps
Sodium hydroxide (40 mL, 6.25 M solution) was added to a stirred solution of 4,6-dichloronicotinic acid ethyl ester (22) (25.95 g, 118 mmol) in 4:1:1 THF:MeOH:water (600 mL). After 30 minutes, the reaction mixture was acidified to pH 2 with concentrated HCl, diluted with 1:1 EtOAc:Et2O and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated. The resulting off-white solid was twice concentrated from toluene to give the desired product (23) as a white solid (21.73 g, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07271178B2 |
| Source dataset | uspto-grants-2007_09 |
| ORD ID | ord-c3dcfaf4540a4128a0b8c41ec1578b57 |
| Source note | uspto-grants-2007_09 |