Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 67051407 | HCID 67051407 | — |
| Solvent | Sulfuric Acid | HCID 1118 | — |
| Product | HCID 58318886 | HCID 58318886 | 84% |
Reaction Steps
3-Chloro-5-(pyrimidin-5-yloxy)benzoic acid (464 mg, 1.85 mmol, 1 eq) was dissolved in methanol (9.3 mL) in a microwave vial and H2SO4 (0.93 mL) was added dropwise. The vial was capped and heated at 75° C. for 3 h. The reaction was cooled to rt and neutralized with 1N NaOH. The reaction was extracted with EtOAc (2×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 414 mg (84%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 9.06 (s, 1H), 8.74 (s, 2H), 7.75 (t, J=1.7 Hz, 1H), 7.65 (t, J=2.2 Hz, 1H), 7.54 (dd, J=1.4, 1.0 Hz, 1H), 3.84 (s, 3H); [M+1]+: 265.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796295B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-d6bb697519b144c2bd8457abb795ff64 |
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| Source note | uspto-grants-2014_08 |
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