Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | 7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile | HCID 57949363 | — |
| Catalyst | Adams' catalyst | HCID 345198 | — |
| Product | HCID 57949729 | HCID 57949729 | 88% |
Reaction Steps
7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (400.0 mg, 1.16 mmol) and PtO2 (26.0 mg, 0.115 mmol) were added to formic acid (2 mL) and the mixture was heated at 60° C. for three hours. The NMR spectrum showed 40% conversion, so PtO2 (50.0 mg) was added to the mixture and it was allowed to stir at 60° C. overnight. After cooling, the mixture was filtered through Celite® and concentrated. Column chromatography (30% EtOAc/Hexanes) provided the title compound as a white solid (357.5 mg, 88%). 1H NMR (300 MHz, CDCl3): δ 10.08 (s, 1H), 7.71 (s, 2H), 7.35 (d, 3H), 7.19 (d, 3H), 4.80 (s, 2H), 4.32 (s, 2H), 2.83 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07968570B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-a5b0d9e0f8c740b3a2d2cd210b8f9a5d |
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| Source note | uspto-grants-2011_06 |
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