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

HRID 423269

반응식

HRID 423269 반응식
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]

참가 물질

5

반응물 2

HCID 666767645-Iodo-N,N-dimethyl-2-nitrobenzamideHCID 178471816HCID 178471816, 화합물

생성물 1

HCID 666758683-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9687531aeefc4263b81c83d83d3846b5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101774B2

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