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

HRID 278088

反応式

HRID 278088 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-31ba064805a246c6b756045b3250a457
出典データセット
uspto-grants-2002_03
特許番号
US06358992B1

関連ノート

読み込み中…