5-Iodo-N,N-dimethyl-2-nitrobenzamide → 3-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester

HRID 423269Notes

Reaction equation

I[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8].[Br-].[CH2:17]([O:19][C:20](=[O:24])[CH2:21][CH2:22][Zn+])[CH3:18]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([O:19][C:20](=[O:24])[CH2:21][CH2:22][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([C:7](=[O:8])[N:9]([CH3:11])[CH3:10])[CH:12]=1)[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

5-Iodo-N,N-dimethyl-2-nitrobenzamide (2.00 g) was dissolved in tetrahydrofuran (20 mL) and bis(triphenylphosphine)palladium(II) dichloride (0.128 g) was added thereto. After cooling down to 0° C., 0.5M 3-ethoxy-3-oxopropylzinc bromide solution (22.5 mL) was added dropwise thereto, the mixture was stirred at room temperature overnight. The reaction solution was concentrated, dissolved in ethyl acetate (100 mL), washed successively with 1N hydrochloric acid (30 mL) and saturated brine (30 mL), and dried over sodium sulfate. Further, the mixture was purified by column chromatography on silica gel (ethyl acetate:hexane=3:2, v/v) to give the title compound (1.52 g) as a brown oil.

Workup

concentrationThe reaction solution was concentrated
dissolutiondissolved in ethyl acetate (100 mL)
washwashed successively with 1N hydrochloric acid (30 mL) and saturated brine (30 mL)
dry with materialdried over sodium sulfate
customFurther, the mixture was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record: ord-9687531aeefc4263b81c83d83d3846b5
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101774B2

Reaction notes

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