Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | m-Toluamide | HCID 69253 | — |
| Reactant | Methyl 2-chloroacetoacetate | HCID 107332 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57804321 | HCID 57804321 | 42.6% |
Reaction Steps
Heat to 120° C. a neat mixture of methyl 2-chloroacetoacetate (914 mL, 7.5 mmol) and 3-methyl-benzamide (676 mg, 5 mmol) and stir at this temperature for 12 hrs. Cool the reaction mixture to room temperature and dilute it with ethyl acetate, wash with saturated sodium bicarbonate solution (3 times), water (twice) and brine, Dry the organic extract over MgSO4 and concentrate. Purify the resulting residue by flash chromatography (elute with 10% ethyl acetate in heptane) to give the title compound as a yellow oil (492 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07576109B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-99426b917f9e47219be76096d3de44bd |
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| Source note | uspto-grants-2009_08 |
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