Methanol → 1-Chloro-4-methyl-6,7,8,9-tetrahydropyridazino[4,5-b]indolizine

HRID 1292070ノート

反応式

HRID 1292070 の反応式
[CH3:1][C:2]1[C:14]2[N:13]3[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)=[CH:7][C:6]=2[C:5](=O)[NH:4][N:3]=1.O=P(Cl)(Cl)[Cl:18].CO.[OH-].[Na+]>C(Cl)Cl>[Cl:18][C:5]1[C:6]2[CH:7]=[C:8]3[N:13]([C:14]=2[C:2]([CH3:1])=[N:3][N:4]=1)[CH2:12][CH2:11][CH2:10][CH2:9]3

参加物

6

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 867526156,7,8,9-Tetrahydro-4-(methyl)pyridazino[4,5-b]indolizin-1-one

生成物 1

HCID 867526161-Chloro-4-methyl-6,7,8,9-tetrahydropyridazino[4,5-b]indolizine収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Compound XI (3.00 g, 15 mmol) was heated under reflux with excess POCl3 (25 mL) until no starting material remained (TLC, silic gel, 5% methanol in methylene chloride), then poured over ice, made basic with aqueous sodium hydroxide and the aqueous phase extracted with methylene chloride to isolate the product. The organic phase was dried (MgSO4), filtered, and evaporated to give a residue which was purified by flash column chromatography (silica gel, 5% methanol in methylene chloride) to give 1-chloro-4-methyl-6,7,8,9-tetrahydropyridazino[4,5-b]indolizine XII (3.00 g, 92%)

後処理

  1. additionpoured over ice
  2. extractionthe aqueous phase extracted with methylene chloride
  3. customto isolate the product
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue which
  8. customwas purified by flash column chromatography (silica gel, 5% methanol in methylene chloride)

出典と根拠

ORDレコード
ord-c0a2361f749148a4a1e86312db4f23d9
出典データセット
uspto-grants-1998_05
特許番号
US05756501

反応ノート

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