3,4,5-Trimethoxybenzaldehyde → HCID 23052527, compound

HRID 1650809Notes

Reaction equation

HRID 1650809 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.Cl.[CH2:16]([O:18][C:19](=[O:22])[CH2:20][NH2:21])[CH3:17].C(=O)([O-])O.[Na+].[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][NH:21][CH2:20][C:19]([O:18][CH2:16][CH3:17])=[O:22]

Participants

7

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 23052527HCID 23052527, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an ethanol solution (50 ml) of 3,4,5-trimethoxybenzaldehyde (2 g, 10 mmol.) and glycine ethyl ester hydrochloride (1.4 g, 10 mmol.) were added sodium hydrogencarbonate (1 g, 12 mmol.) and 5% - palladium on carbon (0.3 g). The reaction solution was stirred for 16 hours at 50° C. under 1 atmosphere pressure of hydrogen. The reaction solution, after cooling, was subjected to filtration to remove the catalyst, and the filtrate was concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (developing solvent: IPE:ethyl acetate=1:1) to afford ethyl N-(3,4,5-trimethoxybenzyl)aminoacetate (2-h, 1.5 g, 47%). Physico-chemical properties and NMR spectrum of this product are shown in Table 4.

Workup

  1. temperatureThe reaction solution, after cooling
  2. filtrationwas subjected to filtration
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe concentrate was purified by means of a silica gel chromatography (developing solvent: IPE:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-449cfffb217b4056a47a230829d8778a
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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