Nitric Acid → Furo[3,2-b]pyridine, 2,3-dihydro-5-nitro-

HRID 2389920Notes

Reaction equation

HRID 2389920 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>S(=O)(=O)(O)O.O>[N+:10]([C:6]1[N:5]=[C:4]2[CH2:3][CH2:2][O:1][C:9]2=[CH:8][CH:7]=1)([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 155348972,3-Dihydrofuro[3,2-b]pyridine

Product 1

HCID 10654607Furo[3,2-b]pyridine, 2,3-dihydro-5-nitro-Yield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 2,3-dihydrofuro[3,2-b]pyridine (32.9 g, 271 mmol) in sulfuric acid (50 mL) was added dropwise a mixed solution of fuming nitric acid (20 mL) and sulfuric acid (20 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was neutralized with 8M aqueous sodium hydroxide solution and diluted with water. The resulting crystals were collected by filtration to give the title compound (37.5 g, yield 83%).

Workup

  1. temperaturecooling
  2. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-5621e300975e47449c669a90da97605b
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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