Acetaldehyde → 3-(Acridin-9-yl)amino-5-(ethylideneamino)phenylmethanol

HRID 1167992Notes

Reaction equation

HRID 1167992 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][C:16]2[CH:17]=[C:18]([CH:20]=[C:21]([CH2:23][OH:24])[CH:22]=2)[NH2:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH:25](=O)[CH3:26]>ClCCl.N1C=CC=CC=1>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][C:16]2[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[C:18]([N:19]=[CH:25][CH3:26])[CH:17]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 3804823-(9-Acridinylamino)-5-hydroxymethylaniline

Product 1

HCID 229948353-(Acridin-9-yl)amino-5-(ethylideneamino)phenylmethanolYield 80.1%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

3-(9-acridinylamino)-5-(hydroxymethyl)aniline was dissolved in dichloromethane/pyridine(1/1, v/v, 40 ml), and thereto acetaldehyde (2.09 g, 47.56 mmol) was added. The resulting mixture was stirred for 5 hours, and the solvent used was removed under the reduced pressure. Then, the resulting product was purified by column chromatography to give the titled compound.

Workup

  1. customthe solvent used was removed under the reduced pressure
  2. customThen, the resulting product was purified by column chromatography

Sources & evidence

ORD record
ord-8721ff2cffa6455aa9491308a5beb31e
Source dataset
uspto-grants-2003_09
Patent number
US06620936B2

Reaction notes

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