Reacción #9356

Ecuación de reacción

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

Disolventes

CHCl3

NEt3

H2O

acetone

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe aqueous layer was extracted with CHCl3
2. 2
   Otrodried
3. 3
   Otroevaporated
4. 4
   Otrothe amide was used without further purification
5. 5
   Extracciónextracted several times with CHCl3
6. 6
   LavadoThe pooled fractions were washed with brine
7. 7
   Secadodried over MgSO4
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated to dryness
10. 10
    OtroThe residue was purified by chromatography on SiO2

Procedimiento

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)

Fuente