Butanoic acid, 4-chloro-4-oxo-, ethyl ester → Ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate

HRID 30689

Reaction equation

HRID 30689 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].Cl[C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 516892Sodium BicarbonateHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 47312066Ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoateYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitrobenzylamine hydrochloride (8.0 g), ethyl 4-chloro-4-oxobutanoate (10.47 g), saturated aqueous sodium hydrogen carbonate (100 ml) and ethyl acetate (100 ml) was stirred at room temperature for 2 hrs. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate (10.3 g, 87%) as colorless prism crystals. melting point: 104-106° C.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-43ba75e21b7741b1b86881fd744ec663
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

Loading…