Nitric Acid → 3-(4-Hydroxy-3-nitrophenyl)pyridine

HRID 393534Notes

Reaction equation

HRID 393534 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:6]=1.O.[OH-].[Na+]>C(O)(=O)C>[N+:1]([C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=2)[CH:16]=[CH:15][C:14]=1[OH:17])([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 153040Phenol, 4-(3-pyridinyl)-

Product 1

HCID 6122253-(4-Hydroxy-3-nitrophenyl)pyridineYield 43.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Nitric acid (60 μL, 1.0 mmol) was added to a solution of 4-pyridin-3-yl-phenol (164 mg, 0.96 mmol) in acetic acid (2.8 mL). The mixture was heated at 60° C. for 30 min and the solution turned orange/brown in color. Upon cooling, water was added (3 mL) and 6 N NaOH (aq) was added until the solution was basic. The solution was extracted with ethyl acetate (3×) and then the aqueous phase was concentrated. The crude residue was washed with boiling methanol to afford 90 mg (43%) of 2-nitro-4-pyridin-3-yl-phenol as an orange solid: mp>300° C., MS (Cl) m/z 217.1 (M+1).

Workup

  1. temperatureUpon cooling
  2. additionwas added until the solution
  3. extractionThe solution was extracted with ethyl acetate (3×)
  4. concentrationthe aqueous phase was concentrated
  5. washThe crude residue was washed with boiling methanol

Sources & evidence

ORD record
ord-c977abf04a23443199c836645abf528c
Source dataset
uspto-grants-2004_10
Patent number
US06809094B2

Reaction notes

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