Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Ethyl bromoacetate | HCID 7748 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 58773023 | HCID 58773023 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11391466 | HCID 11391466 | 63% |
Reaction Steps
To a mixture of (2-methyl-6-nitrophenyl)formamide (180 mg, 1.0 mmol), potassium carbonate (276 mg, 2.0 mmol), potassium iodide (5 mg) and N,N-dimethylformamide (1 mL) a solution of ethyl bromoacetate (184 mg, 1 mmol) in N,N-dimethylformamide (1 mL) was added at room temperature. The mixture was heated at 60° C. for 3 h, then cooled to room temperature. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed with brine and dried over magnesium sulfate. The volatiles were removed in vacuo. The crude product was purified by column chromatography using heptane/ethyl acetate (70:30→50:50) as an eluent affording ethyl N-formyl-N-(2-methyl-6-nitrophenyl)glycinate, 167 mg (63% yield) as an oil. MS (1S) m/z 267 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07645784B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-d9612c0433c7482aa1a531d203f64d19 |
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| Source note | uspto-grants-2010_01 |
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