Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Neopentyl glycol | HCID 31344 | — |
| Reactant | 4-Bromo-6,7-dihydro-8(5H)-isoquinolinone | HCID 71743380 | — |
| Catalyst | p-Toluenesulfonic acid | HCID 6101 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86686023 | HCID 86686023 | 88.9% |
Reaction Steps
A reaction mixture of 4-bromo-6,7-dihydro-5H-isoquinolin-8-one (intermediate B-11 [C], 5.0 g, 22 mmol), 2,2-dimethyl-propane-1,3-diol (2.8 g, 26.5 mmol) and toluene-4-sulfonic acid (85 mg, 0.44 mmol) in toluene (100 mL) was heated at 135° C. for 12 hours. After cooling to room temperature, it was concentrated under reduced pressure to give a residue which was extracted between EtOAc and water. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product (6.1 g, 88.9%) as a light yellow solid. MS: 312.2 & 314.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133158B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-d23a39dd15d946409b8d819fc2e88706 |
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| Source note | uspto-grants-2015_09 |
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