Hydrochloric Acid → HCID 59238226, compound

HRID 1359916Notes

Reaction equation

HRID 1359916 reaction equation
Cl.[Br:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([NH:11]C(=O)C)=[C:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)[CH:4]=1>C(O)(C)C>[Br:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([NH2:11])=[C:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59238256HCID 59238256, compound

Product 1

HCID 59238226HCID 59238226, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Half-concentrated hydrochloric acid (5 mL) is added to a solution of N-[4-bromo-2-(4-ethyl-benzyl)-5-methoxy-phenyl]-acetamide (2.8 g) in isopropanol (20 mL). The solution is heated at reflux temperature for 8 h and then concentrated under reduced pressure to remove most of the alcohol. Aqueous NaHCO3 solution is added to the rest and the resulting mixture is extracted twice with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux temperature for 8 h
  3. concentrationconcentrated under reduced pressure
  4. customto remove most of the alcohol
  5. additionAqueous NaHCO3 solution is added to the rest
  6. extractionthe resulting mixture is extracted twice with ethyl acetate
  7. washThe combined organic extracts are washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-eeed7cb84df54cc28056c5c5beb05544
Source dataset
uspto-grants-2011_02
Patent number
US07879806B2

Reaction notes

Loading…