Acetic Acid → HCID 18516364, compound

HRID 1831740Notes

Reaction equation

HRID 1831740 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:17][CH2:16][CH2:15][C:9]=3[C:10](=[O:14])[NH:11][C:12]=2[CH:13]=1.[Mg].C(O)(=O)C.Cl>CO>[OH:1][CH2:3][CH2:2][C:4]1[CH:5]=[CH:6][C:7]2[CH:8]3[CH2:17][CH2:16][CH2:15][CH:9]3[C:10](=[O:14])[NH:11][C:12]=2[CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5462224Magnesium2×HCID 22052523HCID 22052523, compound

Product 1

HCID 18516364HCID 18516364, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.59 g (2.6 mmol) of 7-oxiranyl-1,2,3,5-tetrahydrocyclopenta[c]-quinolin-4-one in 100 ml of methanol is mixed with 1.26 g (52.0 mmol) of magnesium and 0.06 ml of acetic acid. The batch is stirred for 4 hours at room temperature and mixed with another 0.63 g (26.0 mmol) of magnesium. After 15 hours at room temperature, the reaction mixture is acidified with 200 ml of 10% hydrochloric acid and extracted with ethyl acetate (3×200 ml). The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 0.39 g of product.

Workup

  1. waitAfter 15 hours at room temperature
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-9666e6cf5b884e3298ab6d801b87df81
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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