Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 11345177 | HCID 11345177 | — |
| Solvent | Sulfuric Acid | HCID 1118 | — |
| Product | HCID 11436092 | HCID 11436092 | 97.2% |
Reaction Steps
N-2-Propyn-1-yl-3-(trifluoromethyl)benzamide (Example 370A) (7.0 g, 30.8 mmol) was suspended in sulfuric acid (95˜98%, 15 mL). The mixture was heated at 110° C. for 15 min. After cooling down, ice was added and solution was neutralized with 5N NaOH to pH 7 at 0° C. The mixture was extracted with Et2O three times and the combined organic layers were washed with brine once and dried over MgSO4. Concentration and purification by radial chromatography (0-20% EtOAc-hexanes gradient) afforded the title compound (6.8 g, 97% yield): MS (ES) m/z 228 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07572820B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-a3c26067c6ee4bbea72388805eeba2bd |
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| Source note | uspto-grants-2009_08 |
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