2,4-Dimethoxybenzaldehyde → HCID 64580654, compound

HRID 570726Notes

Reaction equation

HRID 570726 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:14]=1[CH:15]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[CH3:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:14]=1[CH2:15][NH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 126496614-Aminobutyrate ethyl hydrochloride

Product 1

HCID 64580654HCID 64580654, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-aminobutanoate hydrochloride (1.77 g) and 2,4-dimethoxybenzaldehyde (1.75 g) were dissolved in ethanol (50 ml), and the solution was heated under reflux for 1 hr. The mixture was allowed to be cooled to room temperature, sodium triacetoxyborohydride (2.2 g) was added thereto, and the mixture was stirred for 1 hr, and concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution (40 ml), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (2.77 g) as a yellow oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution (40 ml)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7afcde8449f443a1abc3ecbe748dcdf6
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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