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

HRID 1292070노트

반응식

HRID 1292070 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-c0a2361f749148a4a1e86312db4f23d9
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756501

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