Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diethyl Malonate | HCID 7761 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 2-amino-6-chloro-3-nitrobenzoate | HCID 59645472 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59645465 | HCID 59645465 | 76.1% |
Reaction Steps
A mixture of methyl 2-amino-6-chloro-3-nitrobenzoate (4.11 g, 17.8 mmol), diethyl malonate (4.85 g, 30.3 mmol) and solid K2CO3 (powder, 9.11 g, 65.9 mmol) in DMF (71 mL) was heated at 60° C. for 10 h. The reaction mixture was poured into aqueous 1N HCl solution (400 mL) and the resulting solution was extracted with EtOAc (2×250 mL). The combined organic layers were washed with water (3×150 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash chromatography (10-40μ silica gel; hexane:EtOAc 3:1) provided the title compound (4.80 g, 76% yield) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07323567B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-df4076e05c73430bb0b6b8b8d3a2b886 |
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| Source note | uspto-grants-2008_01 |
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