Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | O-Phenylenediamine | HCID 7243 | — |
| Reactant | 4-Hydroxycyclohexanecarboxylic acid | HCID 151138 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 58548623 | HCID 58548623 | 71% |
Reaction Steps
4-Hydroxy-cyclohexanecarboxylic acid (2 g, 13.8 mmol) in a mixture of DMF (4 mL) and pyridine (4 mL) was treated with 1,1-carbonyldiimidazole (2.26 g, 213.8 mmol) at RT and the resulting solution was stirred at 45° C. for 2 h. The mixture was treated with benzene-1,2-diamine (1.5 g, 13.8 mmol) and stirred at RT overnight. After completion, the mixture was concentrated and the obtained residue was treated with glacial acetic acid (20 mL) and heated at 110° C. for 0.5 h. The solution was allowed to cool to RT and concentrated to get a residue, which was purified by flash chromatography on silica gel to provide the title compound (3.0 g, 13.0 mmol, 71% yield) as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08952037B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-2c8e594e2fc246bda7bfdc70264744f9 |
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| Source note | uspto-grants-2015_02 |
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