Potassium Carbonate → 6-Nitroquinolin-2(1H)-one

HRID 501578Notes

Reaction equation

HRID 501578 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14]C(=O)C)[CH:8]=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 597542506-Nitro-2-acetoxyquinoline

Product 1

HCID 8999326-Nitroquinolin-2(1H)-oneYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 46A (210 mg, 0.90 mmol) was dissolved in MeOH (10 mL), K2CO3 was added, and the reaction was stirred at rt for 30 min. The reaction was then concentrated under reduced pressure and subsequently purified by silica gel flash chromatography eluting with 5-10% MeOH/CH2Cl2 (gradient) to give the title compound (162 mg, 94%) as a pink solid. LC/MS m/z 191 [M+H]+.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customsubsequently purified by silica gel flash chromatography
  3. washeluting with 5-10% MeOH/CH2Cl2 (gradient)

Sources & evidence

ORD record
ord-2bf9cc19f3094f8f8fc0e215360b910e
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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