乙酰氯 → N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

HRID 9260

反应方程式

HRID 9260 反应方程式
[C:1]1([NH2:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:12](Cl)(=[O:14])[CH3:13].[NH4+].[Cl-].[O-:18]S([O-])(=O)=O.[Mg+2].[O-][Mn](=O)(=O)=O.[K+]>C(Cl)Cl.C(Cl)(Cl)Cl.CC(C)=O.O.CCN(CC)CC>[O:18]=[C:9]1[C:10]2[C:1]([NH:11][C:12](=[O:14])[CH3:13])=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1

参与物

11

反应物 5

HCID 6367乙酰氯HCID 166711-氨基四氢化萘HCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517氯化铵HCID 516875高锰酸钾

产物 1

HCID 12119265N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

试剂、催化剂与溶剂 5

HCID 180丙酮溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6212三氯甲烷溶剂HCID 6344二氯甲烷溶剂HCID 8471三乙胺溶剂

反应条件

温度
0 °C

实验过程

5,6,7,8-Tetrahydro-naphthalen-1-ylamine (Intermediate J1, commercially available from Aldrich) (5 mL, 35.3 mmol) was dissolved in CH2Cl2 (40 mL) and treated with NEt3 (10 mL) and acetyl chloride (3.8 mL, 53 mmol) at rt for 1 h. The mixture was diluted in CHCl3 and acidified with sat NH4Cl. The aqueous layer was extracted with CHCl3. The organic fractions were combined, dried and evaporated and the amide was used without further purification. The resulting amide (35.3 mmol) in acetone (450 mL) and aqueous MgSO4 (5 g in 28 mL) at 0° C. was treated with KMnO4 (16.8 g, 105 mmol). The mixture was allowed to stir at 0° C. for 2 h. The mixture was diluted with H2O and extracted several times with CHCl3. The pooled fractions were washed with brine and dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography on SiO2 to give N-(8-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl)-acetamide (Intermediate J2) as a yellow oil. (57%, in two 2 steps)

后处理

  1. extractionThe aqueous layer was extracted with CHCl3
  2. customdried
  3. customevaporated
  4. customthe amide was used without further purification
  5. extractionextracted several times with CHCl3
  6. washThe pooled fractions were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by chromatography on SiO2

来源与证据

ORD记录
ord-5a9e347455ad418da520a0da2e094ddc
来源数据集
uspto-grants-2006_08
专利号
US07091232B2

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