HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 16124726, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl 3-amino-4-hydroxybenzoate | HCID 10815 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | PMID26882240-Compound-8 | HCID 625381 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 16124726 | HCID 16124726 | 84.1% |
Reaction Steps
4-Adamantan-1-yl-phenoxy acetic acid (143.2 mg, 0.5 mmol) was dissolved in 5 ml of THF and oxalyl chloride (178.5 mg, 0.11 ml, 1.5 mmol), to which DMF was added. After reacting the mixture at room temperature for 1 hour, 3-amino-4-hydroxy-benzoic acid methyl ester (125.4 mg, 0.75 mmol) and pyridine (0.05 ml) were added thereto. The reaction mixture was reacted at room temperature. Upon completion of the reaction, the reaction mixture was extracted with ethylacetate and NaCl solution, thereafter the organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silicagel column chromatography (N-Hexane: EtOAc:MeOH=6:3:1) to give the target compound as a white solid (183.2 mg, yield: 84.1%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08940936B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-87b65933e07c4629bb7cddb11737a229 |
| Source note | uspto-grants-2015_01 |