Potassium Iodide → 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid

HRID 1477457Notes

Reaction equation

HRID 1477457 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][N:4]=[C:3]1[C:12]([O:14]CC)=[O:13].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C=O)C.O.C(OCC)(=O)C>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[C:3]([C:12]([OH:14])=[O:13])=[N:4]2)=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 23320177Ethyl 4-oxo-1,4-dihydrocinnoline-3-carboxylate

Product 1

HCID 1177769951-(4-Methoxybenzyl)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 4-oxo-1,4-dihydrocinnoline-3-carboxylate (2.0 g), potassium iodide (1.5 g) and potassium carbonate (2.5 g) in DMF (50 mL) was added 1-(chloromethyl)-4-methoxybenzene (1.4 mL), and the mixture was stirred at 70° C. for 14 hr. The reaction mixture was diluted with water and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was dissolved in ethanol-THF (1:1, 30 mL), 1 N aqueous sodium hydroxide solution (15 mL) was added, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with water, neutralized with 1 N hydrochloric acid (15 mL), and the precipitate was collected by filtration, washed with water, and dried to give the title compound (1.1 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe obtained residue was dissolved in ethanol-THF (1:1, 30 mL)
  6. addition1 N aqueous sodium hydroxide solution (15 mL) was added
  7. stirringthe mixture was stirred at room temperature for 6 hr
  8. additionThe reaction mixture was diluted with water
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-eb55fa673b2a458ca59a618af578cb98
Source dataset
uspto-grants-2016_08
Patent number
US09403802B2

Reaction notes

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