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

HRID 30689

반응식

HRID 30689 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-43ba75e21b7741b1b86881fd744ec663
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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