Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl 4-Hydroxybenzoate | HCID 7180 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Chloromethyl-2-methylquinoline hydrochloride | HCID 22227811 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67056944 | HCID 67056944 | 43% |
Reaction Steps
3.6 g (26.3 mmol) of potassium carbonate, 5 g (21.9 mmol) of 4-chloromethyl-2-methylquinoline hydrochloride and 5.2 g (23 mmol) of benzyl 4-hydroxybenzoate are put into solution in 30 ml of dimethylformamide. The reaction medium is heated at 60° C. for 18 h then water is added. After extracting with ethyl acetate, the organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under vacuum. The crude product is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 3.6 g (43%) of benzyl 4-(2-methylquinolin-4-ylmethoxy)benzoate are obtained in the form of a light-yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09115102B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-763d48222841401b88b197eda6650067 |
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| Source note | uspto-grants-2015_08 |
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