Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Malonate | HCID 7761 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 5-Chloro-2-nitrobenzaldehyde | HCID 81123 | — |
| Reactant | Potassium Bicarbonate | HCID 516893 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 70197351 | HCID 70197351 | 85.6% |
Reaction Steps
Potassium hydrogen carbonate (8.12 g) was added to an acetic acid anhydride (18 ml) solution of 5-chloro-2-nitrobenzaldehyde (9.99 g) and diethyl malonate (8.64 g), which was stirred at 110° C. for 2 hours. The reaction mixture was added to iced-water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10) to obtain the entitled compound (15.10 g). 1H-NMR δ: 1.10(3H, t), 1.36(3H, t), 4.15(2H, q), 4.44(2H, q), 7.42(1H, d), 7.52(1H, dd), 8.11(1H, s), 8.18(1H, d).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06329389B1 |
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| Source dataset | uspto-grants-2001_12 |
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| ORD ID | ord-e115e0c1cda9438e806031d0d4478649 |
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| Source note | uspto-grants-2001_12 |
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