Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Methyl 1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate | HCID 89813003 | — |
| Product | HCID 89812860 | HCID 89812860 | 70% |
Reaction Steps
To a mixture of 1-bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (2.0 g, 5.34 mmol) in 16.2 mL of N-methylpyrrolidone was heated in a 130° C. oil bath for 2 h. After cooled, the reaction mixture was poured into a mixture of 100 mL of water (containing 5% conc. NH4OH) and EtOAc (100 mL). It was vigorously stirred at room temperature for 30 min, then was acidified by conc. HCl solution until two phases became clear. Organic layer was washed with water, brine and dried over MgSO4. It was filtered and concentrated. Crude product was triturated with MeOH and white solid was collected to provide the title compound 1.20 g (3.75 mmol) in 70% yield. LC-MS ESI+: 321.31 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409892B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-8d982f50483b43a69888246f7cfd6603 |
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| Source note | uspto-grants-2016_08 |
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