Diethyl Malonate → 3-(4-Nitrophenyl)propanoic acid

HRID 880411

반응식

HRID 880411 반응식
[C:1]([O:9]CC)(=[O:8])[CH2:2][C:3](OCC)=O.[N+:12]([C:15]1[CH:22]=[CH:21][C:18](CBr)=[CH:17][CH:16]=1)([O-:14])=[O:13].[H-].[Na+].[OH-].[Na+]>C1COCC1.O.C(O)C>[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:3][CH2:2][C:1]([OH:9])=[O:8])=[CH:17][CH:16]=1)([O-:14])=[O:13]

참가 물질

8

반응물 4

HCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromide

생성물 1

HCID 855263-(4-Nitrophenyl)propanoic acid

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Alkylation of diethyl malonate with 4-nitrobenzyl bromide using sodium hydride in THF, followed by ester hydrolysis with sodium hydroxide in water and ethanol, then heating the resulting diacid to its melting point causing decarboxylation gives 3-(4-nitro-phenyl)-propionic acid. Conversion to the acid chloride with thionyl chloride in DCM and coupling with 2-amino-4,6-dimethylpyridine affords N-(4,6-dimethyl-pyridin-2-yl)-3-(4-nitro-phenyl)-propionamide. Amide reduction with borane-dimethylsulfide in THF at reflux, methylation of the resulting amine with methyl iodide and sodium hydride in THF and finally catalytic hydrogenation over Raney nickel in methanol gives the required aniline.

출처 및 근거

ORD 기록
ord-1195b865c2c54e96bed8595ae2ea32b4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993574B2

연결된 노트

불러오는 중…