Hydrochloric Acid → HCID 55264285, compound

HRID 1661528Notes

Reaction equation

HRID 1661528 reaction equation
Cl.[O:2]=[C:3]1[C:7]2[CH:8]=[CH:9][C:10]([NH:12]C(=O)C)=[CH:11][C:6]=2[O:5][CH2:4]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO>[NH2:12][C:10]1[CH:9]=[CH:8][C:7]2[C:3](=[O:2])[CH2:4][O:5][C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 19959496HCID 19959496, compound

Product 1

HCID 55264285HCID 55264285, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 ml of 1 N hydrochloric acid are added to a solution of 500 mg (2.62 mmol) of N-(3-oxo-2,3-dihydro-1-benzofuran-6-yl)acetamide in 5 ml of methanol, and the mixture is heated under reflux for one hour. After cooling, the mixture is added to a mixture of ice-water, saturated sodium bicarbonate solution and ethyl acetate. The organic phase is separated off, washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. 318 mg (61% of theory) of the target compound result as brown powder with a purity of 75%.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for one hour
  3. temperatureAfter cooling
  4. customThe organic phase is separated off
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custom318 mg (61% of theory) of the target compound result as brown powder with a purity of 75%

Sources & evidence

ORD record
ord-7d82e3e0d54840a3bd21d60e2591645f
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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