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

HRID 2281457Notes

Reaction equation

HRID 2281457 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-af8767eb9ab7486dafd476ab1866d1e3
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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