Acetyl chloride → N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

HRID 9260

反応式

HRID 9260 の反応式
[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

参加物

11

反応物 5

HCID 6367Acetyl chlorideHCID 166715-TetralinylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 516875Potassium Permanganate

生成物 1

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

試薬・触媒・溶媒 5

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-5a9e347455ad418da520a0da2e094ddc
出典データセット
uspto-grants-2006_08
特許番号
US07091232B2

関連ノート

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