Benzyl Alcohol → 2-benzyloxy-5-nitro-pyridine

HRID 1665626Notes

Reaction equation

HRID 1665626 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2956762-benzyloxy-5-nitro-pyridineYield 28.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl alcohol (682 mg, 6.3 mmol), 18 crown ether (2.5 g, 9.4 mmol) and KOH (637 mg, 11.3 mmol) were added to a solution of 2-chloro-5-nitro-pyridine (1 g, 6.3 mmol) in toluene (15 mL) and the reaction mixture was maintained at 80° C. for 2 hours, then diluted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and evaporated. The residue was purified by column chromatography using neutral alumina (2% ethyl acetate in hexane) to afford 410 mg (28%) of 2-benzyloxy-5-nitro-pyridine. LCMS: 231.07 (M+1)+, 98.4%

Workup

  1. washThe organic layer was washed with brine solution
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0afc4471aa654ba89dcbb3cfeb33450b
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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