Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 67362572 | HCID 67362572 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 67377290 | HCID 67377290 | 70% |
Reaction Steps
To a solution of 6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (intermediate 1c) (0.8 g, 3.16 mmol) in MeOH (15 mL), KOH (53 mg, 0.94 mmol) followed by PhCHO (2.6 g, 24.5 mmol) were added. The reaction mixture was heated to 70-80° C. for 12 h. The solids were filtered and dried in vacuo to afford the title compound as a light yellow solid (0.75 g, 70%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 12.07 (s, 1H), 8.05 (s, 1H), 7.64 (d, J=13.0 Hz, 2H), 7.54 (d, J=7.0 Hz, 2H), 7.49-7.46 (m, 2H), 7.41 (d, J=7.5 Hz, 1H), 3.21-3.18 (m, 2H), 3.05-3.02 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08987319B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-d777fa8b5876497794745cb7fb4c5535 |
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| Source note | uspto-grants-2015_03 |
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