Sodium hydride → 3-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

HRID 1747812ノート

反応式

HRID 1747812 の反応式
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[H-].[Na+].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[C:7](=[O:8])[C:6]([O:9][CH3:10])=[CH:5][N:4]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[N:3]=1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178493809HCID 178493809、化合物

生成物 1

HCID 895861593-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

3-Chloro-5-methoxypyridazin-4-ol (0.20 g) was dissolved in DMF (3.1 mL), NaH (0.0595 g, 60%, in oil) and tetrabutylammoniumiodide (0.0916 g) were added at 0° C., and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added (bromomethyl)cyclopropane (0.138 mL) at 0° C., and the mixture was stirred at 0° C. for 2.5 hr, at room temperature for 1 day and at 40° C. for 20 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) to give the title compound (0.136 g).

後処理

  1. stirringthe mixture was stirred at 0° C. for 2.5 hr, at room temperature for 1 day and at 40° C. for 20 hr
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-ce6e91da4f2344778e44fd50e482bb17
出典データセット
uspto-grants-2015_10
特許番号
US09150588B2

反応ノート

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