Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 2-Chloronicotinoyl chloride | HCID 2774541 | — |
| Reactant | 1,1,3-Trimethylindan-4-amine | HCID 11217541 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 14535909 | HCID 14535909 | 47% |
Reaction Steps
To a solution of 2.6 g (14.8 mmol) of 2-chloronicotinic acid chloride in 15 ml of sulforan was added 2.6 g (46.4 mmol) of potassium fluoride, and the mixture was stirred under heating at 155° C. for 6 hours. After cooling, precipitated crystals were filtered out. The filtrate was added dropwise to a solution of 2 g (11.4 mmol) of 4-amino-1,1,3-trimethylindane and 1.6 g (15.8 mmol) of triethylamine in 10 ml of toluene under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was then added with 30 ml of toluene, washed with water, dried over Glauber's salt and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=4/1) to obtain 1.6 g of oil (Compound No. 9 shown in Table 2) in a yield of 47%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04840959 |
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| Source dataset | uspto-grants-1989_06 |
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| ORD ID | ord-94c310c205e049c09c831574fe58c834 |
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| Source note | uspto-grants-1989_06 |
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