Sodium Hydroxide → HCID 19837289, compound

HRID 477045Notes

Reaction equation

HRID 477045 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1.[OH-].[Na+].C(=O)([O-])O.[Na+]>Br>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 19837284HCID 19837284, compound

Product 1

HCID 19837289HCID 19837289, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

1.235 g of 3-(4-methoxy-2-nitrophenyl)pyridine was dissolved in 100 ml of a 47% aqueous solution of hydrogen bromide, and the solution was stirred at a bath temperature of 120° C. for 8 hours. After cooling, the reaction mixture was adjusted to pH 3-4 with a 50% aqueous solution of sodium hydroxide, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The solvent was evaporated, and the crude crystals were recrystallized from ethyl acetate to give 477 mg of 3-(4-hydroxy-2-nitrophenyl)pyridine. The recrystallization mother liquor was subjected to silica gel column chromatography, and the column was eluted with a 50:1 mixture of chloroform and ethanol. The solvent was evaporated to give 331 mg of the above compound. The total amount of the above compound was 808 mg (yield 69.7%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe solvent was evaporated
  4. customthe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b8e717689493432f999e542f90698ac5
Source dataset
uspto-grants-1989_12
Patent number
US04886822

Reaction notes

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