HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Tetralone → 4-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Tetralone | HCID 10724 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | Tert-butyl 2-(4-(aminosulfonyl)-2-nitrophenyl)hydrazinecarboxylate | HCID 22730367 | — |
| Solvent | Trifluoroacetic acid methylene chloride | HCID 21863450 | — |
| Product | 4-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide | HCID 9612165 | — |
Reaction Steps
A room temperature solution of Example 73A (145 mg,0.44 mmol) in 1:1 TFA/dichloromethane (10 mL) was stirred for 4 hours and concentrated. The concentrate was dissolved in ethanol (2 mL), treated with 3,4-dihydro-1(2H)-naphthalenone (8.2 mg, 0.06 mmol) and pyridinium p-toluenesulfonate (2 mg, 0.008 mmol), heated to reflux, stirred for 2 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 359 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07504512B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-e8120fa171c24b559a2c6215295f49b4 |
| Source note | uspto-grants-2009_03 |