Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-chloro-N,N-dimethylacetamide | HCID 75886 | — |
| Reactant | Tilnoprofenic acid | HCID 3080818 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tilnoprofen Arbamel | HCID 164072 | 90.1% |
Reaction Steps
Under a nitrogen atmosphere, 5.4 g of α,2-dimethyl-5H-[1]-benzopyrano [2,3-b]pyridine-7-acetic acid is dissolved in 22 ml of dimethylformamide, whereafter 1.9 g of potassium carbonate and 2.7 g of N,N-dimethyl-2-chloroacetamide are added, and the mixture is stirred at 75° C. for 2 hours. Under cooling with ice, 50 ml of water is added to the resulting reaction mixture. The precipitated crystals are collected by filtration and washed with water, and then recrystallized from isopropyl alcohol to obtain 6.4 g of N,N-dimethylcarbamoylmethyl α,2-dimethyl-5H-[1]benzopyrano[2,3-b]-pyridine-7acetate as white crystals having a melting point of 150° to 151° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04808593 |
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| Source dataset | uspto-grants-1989_02 |
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| ORD ID | ord-bfbfe8095ec74ec293339134743d34ef |
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| Source note | uspto-grants-1989_02 |
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