Ethyl 3-(2,4-dinitrophenyl)propanoate → 7-amino-3,4-dihydro-1H-quinolin-2-one

HRID 641930Notes

Reaction equation

HRID 641930 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14][C:15]([O:17]CC)=O)([O-])=O.[H][H]>CO.[Pd]>[NH2:10][C:8]1[CH:9]=[C:4]2[C:5]([CH2:13][CH2:14][C:15](=[O:17])[NH:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 17352660Ethyl 3-(2,4-dinitrophenyl)propanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 52002427-amino-3,4-dihydro-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Into a 100 mL 3-necked round bottom flask was placed a solution of ethyl 3-(2,4-dinitrophenyl)propanoate (1.5 g, 5.60 mmol) in methanol (20 mL). To the mixture was added Pd/C (0.5 g). Hydrogen gas was passed through. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 30° C. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 0.5 g (55%) of 7-amino-3,4-dihydroquinolin-2(1H)-one as a green-yellow solid.

Workup

  1. customInto a 100 mL 3-necked round bottom flask was placed
  2. customto react
  3. filtrationA filtration
  4. concentrationThe filtrate was concentrated by evaporation under vacuum
  5. customa rotary evaporator
  6. customThis resulted in 0.5 g (55%) of 7-amino-3,4-dihydroquinolin-2(1H)-one as a green-yellow solid

Sources & evidence

ORD record
ord-f3b7dde3f73e4272be022b5e40f1d2a8
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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