p-Aminoacetophenone → HCID 53405747, compound

HRID 1588770Notes

Reaction equation

HRID 1588770 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1>CO.[OH-].[Na+]>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH:11]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[O:10])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7468p-AminoacetophenoneHCID 115693-Methoxybenzaldehyde

Product 1

HCID 53405747HCID 53405747, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of p-aminoacetophenone (14.9 g, 0.11 mol) and m-anisaldehyde (10.0 g, 73 mmol) in methanol (500 ml) and 1N NaOH (260 ml) was stirred at room temperature overnight. The precipitate was collected, the filtrate was concentrated to 300 ml and the new precipitate was collected. The combined solids were recrystallized from isopropanol to give present title product as a yellow solid (10.4 g, 56%).

Workup

  1. customThe precipitate was collected
  2. concentrationthe filtrate was concentrated to 300 ml
  3. customthe new precipitate was collected
  4. customThe combined solids were recrystallized from isopropanol

Sources & evidence

ORD record
ord-1704efc21486415a819e76c05bc9d377
Source dataset
uspto-grants-1993_06
Patent number
US05223522

Reaction notes

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