HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium hydroxide, monohydrate → 6-Cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | Methyl 6-cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate | HCID 67289723 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Catalyst | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-Cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid | HCID 67287399 | 39% |
Reaction Steps
To a solution of methyl 6-cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.061 g, 0.120 mmol) in THF (2 mL) was added LiOH—H2O (0.239 mL, 0.239 mmol) and added a few drops of methanol to ensure a homogeneous solution. The reaction was stirred at ambient temperature for 3 hours. A few drops of acetic acid were added to the reaction and the solution concentrated to a yellow/white solid. The crude material was purified by silica gel column chromatography using 5% methanol/dichloromethane+0.1% acetic acid to provide the desired product (0.023 g, 39%). MS (APCI)=496.3 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08785445B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-a7b6436b49644e30b9e304e6026ad670 |
| Source note | uspto-grants-2014_07 |