Acetic Acid → HCID 15429323, compound

HRID 1831733Notes

Reaction equation

HRID 1831733 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[CH2:19][CH2:18][CH2:17][C:11]=3[C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1.[Mg].C(O)(=O)C.Cl>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[CH:10]3[CH2:19][CH2:18][CH2:17][CH:11]3[C:12](=[O:16])[NH:13][C:14]=2[CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5462224Magnesium2×HCID 15429322HCID 15429322, compound

Product 1

HCID 15429323HCID 15429323, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.32 g (5.3 mmol) of 7-(2-furanyl)-1,2,3,5-tetrahydrocyclo-penta[c]quinolin-4-one in 300 ml of methanol is mixed with 2.58 g (10.6 mmol) of magnesium and 0.06 ml of acetic acid. After 15 hours at room temperature, another 1.29 g (5.3 mmol) of magnesium is added to it. The batch is stirred for 15 hours at room temperature, treated with 10% hydrochloric acid (500 ml) and extracted with ethyl acetate (3×300 ml). The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 0.49 g of product.

Workup

  1. extractionextracted with ethyl acetate (3×300 ml)
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-1d2535b055754bb483792cebbc524ef0
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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