2-Hydroxy-4-Methoxybenzaldehyde → HCID 178515945, compound

HRID 2227146Notes

Reaction equation

HRID 2227146 reaction equation
C(N(CC)[C:4]1[CH:5]=[C:6]([OH:17])[C:7](=[CH:15][CH:16]=1)[CH:8]=[N:9][CH2:10][C:11](C)([NH2:13])C)C.CO[C:22]1[CH:23]=[C:24]([OH:30])[C:25](=[CH:28][CH:29]=1)[CH:26]=O.C(OCC)(=O)C.CO>C(O)C>[CH:16]1[CH:4]=[CH:5][C:6](=[O:17])/[C:7](=[CH:8]/[NH:9][CH2:10][CH2:11][NH:13]/[CH:26]=[C:25]2/[CH:28]=[CH:29][CH:22]=[CH:23][C:24]/2=[O:30])/[CH:15]=1

Participants

5

Reactant 3

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 21584119Ethylacetate methanolHCID 135744196HCID 135744196, compound

Product 1

HCID 178515945HCID 178515945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 13.6 g (0.0517 mol) of N-Mono[4-(diethylamino)salicylidene]-2-methylpropane-1,2-diamine from Example 1 in 50 ml of ethanol is heated with stirring at 50° C. until a clear solution is obtained. 7.87 g (0.0517 mol) of 4-methoxysalicylaldehyde (solid) are added and the mixture is heated at reflux for 2 h. After that time the reaction is complete (TLC monitoring, ethyl acetate/methanol 9:1). Thereafter the reaction solution is carefully concentrated and the residue is dried under a high vacuum. The crude product obtained comprises 20 g of a dark red oil, which slowly solidifies. Purification is by column chromatography (eluent mixture: ethyl acetate/methanol 9:1). The asymmetrically substituted salen derivative is isolated as the diastereomer mixture (structures I and II). Yield: 7 g, reddish oil (34%). The product is characterized by 1H and 13C NMR spectroscopy.

Workup

  1. temperatureis heated
  2. customis obtained
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 2 h
  5. concentrationThereafter the reaction solution is carefully concentrated
  6. customthe residue is dried under a high vacuum
  7. customThe crude product obtained
  8. customPurification

Sources & evidence

ORD record
ord-6407da8ad75e4163a130cb36e8700f78
Source dataset
uspto-grants-2002_07
Patent number
US06413926B2

Reaction notes

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