Hydrochloric Acid → HCID 13463080, compound

HRID 1161039Notes

Reaction equation

HRID 1161039 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]C(=O)C)=[C:6]([CH2:14][CH2:15][CH3:16])[C:5]=1[OH:17])(=[O:3])[CH3:2].Cl>C(O)C>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[C:5]([OH:17])[C:6]=1[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2775203N1-(4-acetyl-3-hydroxy-2-propylphenyl)acetamide

Product 1

HCID 13463080HCID 13463080, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To N1-(4-acetyl-3-hydroxy-2-propylphenyl)acetamide (1.0 g, 4.3 mmol) in absolute ethanol (15 mL) is added 6N HCl (15 mL). The reaction mixture is refluxed for 3 h. The reaction mixture is cooled to RT and quenched into saturated aqueous NaHCO3. The mixture is extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried over Na2SO4 and concentrated. Obtained is the title compound (827 mg, 99%). LC-MS (m/e): 194 (M+1).

Workup

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. customquenched into saturated aqueous NaHCO3
  3. extractionThe mixture is extracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customObtained

Sources & evidence

ORD record
ord-b390048c3e764fba8d0c38f0ae89c50f
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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