Potassium Iodide → HCID 11391466, compound

HRID 1991187Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 60 °C

Procedure

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].

Workup

additionwas added at room temperature
temperaturecooled to room temperature
customThe mixture was partitioned between water and ethyl acetate
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customThe volatiles were removed in vacuo
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-d9612c0433c7482aa1a531d203f64d19
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645784B2

Reaction notes

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