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

Temperature

0 °C

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)

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

ORD record

ord-ed230dc0a96e4d2596f9049f5ff18873

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063087B2