Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 12811134 | HCID 12811134 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 12811139 | HCID 12811139 | 75% |
Reaction Steps
To a mixture of ethyl 4-methyl-6-(4-aminophenyl)-2-pyridinecarboxylate hydrochloride (6 g), water (150 ml), sodium hydrogen carbonate (6 g) and ethyl acetate (150 ml) is added under ice-cooling with agitation benzyloxycarbonyl chloride (4.2 g), and the mixture is agitated for 45 minutes. The reaction mixture is made acidic with diluted hydrochloric acid, and the resulting crystals are collected by filtration, washed with water and dried. The organic layer is separated from the filtrate, washed with water and dried, and then the solvent is distilled off therefrom under reduced pressure. To the resulting residue is added ethyl acetate, and the precipitated crystals are collected by filtration and combined with the crystals obtained above to give ethyl 4-methyl-6-(4-benzyloxycarbonylaminophenyl)-2-pyridinecarboxylate (6 g). M.P. 184°-185° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04332809 |
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| Source dataset | uspto-grants-1982_06 |
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| ORD ID | ord-12e0c29ea12c49d19f8ddd921f0c03a2 |
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| Source note | uspto-grants-1982_06 |
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