p-Aminoacetophenone → HCID 53405747, compound

HRID 346212Notes

Reaction equation

HRID 346212 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-20c6504a91cd49b0b339608884a528b6
Source dataset
uspto-grants-1991_10
Patent number
US05061717

Reaction notes

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