Hydrochloric Acid → Coumaranone

HRID 1749923Notes

Reaction equation

HRID 1749923 reaction equation
C([O:4][C:5]1[C:9]2[CH:10]=[C:11](Cl)[CH:12]=[C:13](CN3CCN(C)CC3)[C:8]=2[O:7][CH:6]=1)(=O)C.O.Cl>CO>[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:5](=[O:4])[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 71278908HCID 71278908, compound

Product 1

HCID 23556CoumaranoneYield 141%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-chloro-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3-yl acetate (0.12 g, 0.37 mmol) in methanol (8.0 mL) was added with water (2.0 mL) and concentrated hydrochloric acid (0.20 mL), and the mixture was stirred at 80° C. for 4 hours. The solvent was evaporated under reduced pressure, then the residue was dissolved in ethyl acetate, and the solution was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluted with chloroform/methanol (99:1→95:5)) to obtain 5-chloro-7-[(4-methylpiperazin-1-yl)methyl)]benzofuran-3(2H)-one (0.070 g, 67%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with chloroform/methanol (99:1→95:5))

Sources & evidence

ORD record
ord-ff28569b29eb4c7f8639049478076f4f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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