Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | HCID 68862599 | HCID 68862599 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68863981 | HCID 68863981 | 32.9% |
Reaction Steps
A mixture of methyl 2-amino-1-naphthoate (0.7 g, 3.48 mmol) in acetonitrile (15 mL) was treated with N-chlorosuccinimide (490 mg, 3.65 mmol), stirred at 60° C. for 7 hours, cooled to room temperature, stirred overnight, concentrated, and purified by flash column chromatography on silica gel with 10% ethyl acetate/n-hexane to provide the desired product (270 mg). MS (ESI(−)) m/e 234 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.13 (s, 1H), 8.10 (d, 1H), 7.75 (d, 1H), 7.46 (dt, 1H), 7.26 (dt, 1H), 6.62 (s, 2H), 3.95 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07491718B2 |
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| Source dataset | uspto-grants-2009_02 |
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| ORD ID | ord-9ea6275c229a4a64b1fe7f0d65311244 |
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| Source note | uspto-grants-2009_02 |
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