Hydrochloric Acid → HCID 21832172, compound

HRID 1901190Notes

Reaction equation

HRID 1901190 reaction equation
[ClH:1].Cl.N[C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.N([O-])=O.[Na+].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21]>O.CC(C)=O>[Cl:1][CH:20]([CH2:21][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)[C:19]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 218321461-(4-Aminophenoxy)propan-2-one hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 21832172HCID 21832172, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

50 ml of 35% w/v aqueous hydrochloric acid were added to a mixture of 20 g of the 1-(4-aminophenoxy)-propan-2-one hydrochloride [prepared as described in step (a) above] and 400 ml of acetone, and then a solution of 12 g of sodium nitrite in 20 ml of water was added dropwise to the resulting mixture, whilst ice-cooling; the mixture was then stirred at the same temperature for 20 minutes. At the end of this time, 130 g of ethyl acrylate and then 3.2 g of cuprous oxide were added in portions to the mixture, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated by evaporation under reduced pressure, and the concentrate was mixed with water and ethyl acetate. The ethyl acetate layer was separated, washed with water and dried over anhydrous sodium sulfate; the solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 11.3 g of the title compound having an Rf=0.31 (thin layer chromatography over silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  4. additionthe concentrate was mixed with water and ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was then removed by distillation under reduced pressure
  9. customThe resulting residue was purified by column chromatography through silica gel
  10. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-5a451e4fce6f440ab056f620d6ad2d20
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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