6-Methyl-2-nitropyridin-3-ol → HCID 23078448, compound

HRID 228744Notes

Reaction equation

HRID 228744 reaction equation
[N+:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([CH3:11])[N:5]=1)([O-:3])=[O:2].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH3:26])[N:16]=[CH:15][CH:14]=[C:13]2[O:10][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[N:5][C:6]([CH3:11])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 848016-Methyl-2-nitropyridin-3-olHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 23078448HCID 23078448, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
130 °C

Procedure

2-Nitro-6-methylpyridin-3-ol (4.1 g), 4-chloro-6,7-dimethoxyquinoline (2 g), and 4-(N,N-dimethylamino)-pyridine (3.3 g) were dissolved in 1,2-dichlorobenzene (90 ml) to prepare a solution which was then stirred at 130° C. overnight. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. A 1 N aqueous sodium hydroxide solution was added to the residue, the mixture was extracted with ethyl acetate, and the ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-acetone to give the title compound (732 mg, yield 24%).

Workup

  1. customto prepare a solution which
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionA 1 N aqueous sodium hydroxide solution was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b693206806344fd1913f40fec66b09fa
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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