Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 1,1,3-Trimethylindan-4-amine | HCID 11217541 | — |
| Reactant | HCID 178524895 | HCID 178524895 | — |
| Catalyst | Pyridine | HCID 1049 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 14698781 | HCID 14698781 | 61% |
Reaction Steps
A mixture of 0.5 g (3.57 mmols) of 3-hydroxypyrazine-2-carboxylic acid, 3 ml of phosphorus oxychloride, and one drop of pyridine was refluxed for 3 hours. The resultant reaction solution was distilled to remove excess phosphorus oxychloride. To the residue 5 ml of ethyl acetate was added. The solution was added dropwise to 10 ml of an ethyl acetate solution of 0.53 g (3 mmols) of 4-amino-1,1,3-trimethylindane and 0.4 g (3.96 mmols) of triethylamine. The resultant mixture was stirred at room temperature for 2 hours and then sequentially washed with water, sodium hydrogen carbonate, water, and a saturated brine. The washed solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/4), to obtain 0.58 g of light yellow crystals (Compound No. 10 shown in Table 5). The yield was 61%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04914097 |
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| Source dataset | uspto-grants-1990_04 |
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| ORD ID | ord-8ee59e4735c6433ba397648e649a99a2 |
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| Source note | uspto-grants-1990_04 |
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