Réaction #9356

Équation de réaction

NH4Cl

acetyl chloride

MgSO4

KMnO4

5,6,7,8-Tetrahydro-naphthalen-1-ylamine

→

N-(8-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl)-acetamide

Solvants

CHCl3

NEt3

H2O

acetone

CH2Cl2

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous layer was extracted with CHCl3
2. 2
   Autredried
3. 3
   Autreevaporated
4. 4
   Autrethe amide was used without further purification
5. 5
   Extractionextracted several times with CHCl3
6. 6
   LavageThe pooled fractions were washed with brine
7. 7
   Séchagedried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated to dryness
10. 10
    AutreThe residue was purified by chromatography on SiO2

Mode opératoire

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)

Source