Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | HCID 59377985 | HCID 59377985 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59378012 | HCID 59378012 | 50.6% |
Reaction Steps
To a solution of 2-(5-amino-2-chloro-4-methyl-phenyl)-malonic acid diethyl ester (0.50 g, 2.17 mmol) in DMSO (3 ml) and water (0.078 ml) was added, followed by lithium chloride (0.138 g, 3.26 mmol). The mixture was heated to 170° C. for three hours, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 8:2) gave 0.250 g (50%) of (5-amino-2-chloro-4-methyl-phenyl)-acetic acid ethyl ester as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08288552B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-ef8441fe26b44e5fbfc83219bea32b1d |
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| Source note | uspto-grants-2012_10 |
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