Ammonium formate → ethyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

HRID 2281457노트

반응식

HRID 2281457 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9](=[O:20])[CH2:8][CH2:7]2)([O-])=O.C([O-])=O.[NH4+]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9](=[O:20])[CH2:8][CH2:7]2

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 43446515ethyl 2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

생성물 1

HCID 43382557ethyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate수율 31%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a suspension of 1 ethyl 2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate in EtOH (10 mL) and H2O (5 mL) was added ammonium formate (1.5 g, 23.8 mmol) and Fe (0.3 g, 5.4 mmol). After stirring at reflux for 2 h, the black mixture was filtered, the filtrate was diluted with EtOAc and water, EtOAc layer was separated and the aqueous layer was further extracted with EtOAc, organic layers were combined, dried over Na2SO4, and was concentrated in vacuo to provide ethyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate (0.2 g, 31%).

후처리

  1. temperatureat reflux for 2 h
  2. filtrationthe black mixture was filtered
  3. additionthe filtrate was diluted with EtOAc and water, EtOAc layer
  4. customwas separated
  5. extractionthe aqueous layer was further extracted with EtOAc, organic layers
  6. dry with materialdried over Na2SO4
  7. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-af8767eb9ab7486dafd476ab1866d1e3
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139581B2

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