[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:11][CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[CH:12]([N:11]([C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:13]
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].
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