Pyridine → Methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate

HRID 1108702

반응식

HRID 1108702 반응식
[CH3:1][N:2]([CH3:18])/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].N1C=CC=CC=1.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28]>O1CCCC1.O>[CH3:18][N:2]([CH:3]=[C:4]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])[C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH3:1]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

생성물 1

HCID 54551046Methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To a stirred mixture of methyl (E)-4-[2-(dimethylamino)vinyl]-3-nitrobenzoate (500 mg), which was prepared by the method of Brown et al. described in Journal of Medicinal Chemistry, vol. 35, page 2419 (1992), and pyridine (0.16 ml) in tetrahydrofuran (3 ml) was added butyryl chloride (0.21 ml) at 20° C. The reaction mixture was stirred at 40° C. for 24 hours and 50° C. for 4 hours. After cooled to 20° C., the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:1) to give methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate (426 mg) as colorless amorphous.

후처리

  1. customwas prepared by the method of Brown et al.
  2. temperatureAfter cooled to 20° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:1)

출처 및 근거

ORD 기록
ord-1fcbf5fece15453f9a552fa4c964373e
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069156

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