Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Butyryl chloride | HCID 8855 | — |
| Reactant | Methyl 2-amino-4-methylbenzoate | HCID 11205965 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57443334 | HCID 57443334 | 103.9% |
Reaction Steps
To a 0° C. solution of 2-amino-4-methyl-benzoic acid methyl ester (1.5 g, 9.0 mmol) and triethylamine (1.4 g, 13.5 mmol) in methylene chloride (30.0 mL) is added butyryl chloride (1.2 g, 10.8 mmol) dropwise. The mixture is stirred at 0° C. for 30 min and is quenched with saturated sodium bicarbonate (10 mL). The organic phase is washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as syrup (2.2 g, 100%). LC-ES/MS m/e 236.3 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07846960B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-af7ddd3bcafd4b258c2b8e36aab3244c |
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| Source note | uspto-grants-2010_12 |
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