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

HRID 560130Notes

Reaction equation

HRID 560130 reaction equation
[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

Participants

11

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

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 EC was treated with KMnO4 (16.8 g, 105 mmol). The mixture was allowed to stir at 0 EC 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)

Workup

  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

Sources & evidence

ORD record
ord-c2b0605e076f4de1b516d87486314259
Source dataset
uspto-grants-2011_11
Patent number
US08063086B2

Reaction notes

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