Sodium Bicarbonate → 5-Amino-1,2-dihydroquinolin-2-one

HRID 2182661Notes

Reaction equation

HRID 2182661 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:12]C)=[N:7]2.C([O-])(O)=O.[Na+]>Cl.O>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 122830362-Methoxyquinolin-5-amine

Product 1

HCID 157190785-Amino-1,2-dihydroquinolin-2-oneYield 50.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

1.45 g (8.3 mmol) of 5-amino-2-methoxyquinoline is refluxed in 29 ml of 6N HCl for 4.5 hours. It is allowed to cool to room temperature, diluted with water, made basic with NaHCO3, extracted with ethyl acetate, the combined organic extracts are dried (Na2SO4) and concentrated by evaporation. Purification of the residue by chromatography on silica gel with hexane-ethyl acetate yields 670 mg of a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customPurification of the residue by chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-0108357a918c47d997655ad57b9e657b
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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