Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2,4-Difluoro-α-hydroxy-5-methoxybenzeneacetonitrile | HCID 57942911 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 68436566 | HCID 68436566 | — |
Reaction Steps
To 98B (427 mg, 2.1 mmol) in anhydrous diethyl ether (10 mL) at 0° C. was added MeOH (0.87 mL, 10 eq.) and 4.0 N HCl in dioxane (4.2 mL, 16.8 mmol). The mixture was stirred at 4° C. for 24 h. Solvent was removed to give methyl 2-(2,4-difluoro-5-methoxyphenyl)-2-hydroxyacetimidate HCl salt. To this salt in CH2Cl2 (8.0 mL) was added H2O (8.0 mL). The mixture was stirred at rt for 30 min, then extracted with CH2Cl2 (2×50 mL). The combined organic extracts were dried and concentrated to give product 98C (493 mg, 99% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.41 (d, J=4.83 Hz, 1H) 3.72 (s, 3H) 3.80 (s, 3H) 5.32 (d, J=4.83 Hz, 1H) 6.78-6.84 (m, 1H) 6.90 (dd, J=9.01, 6.81 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07622585B2 |
|---|
| Source dataset | uspto-grants-2009_11 |
|---|
| ORD ID | ord-76110516a9794e1593957c2a0c102212 |
|---|
| Source note | uspto-grants-2009_11 |
|---|