HCID 58150279, compound → 3-(2-Hydroxyphenyl)pyridine

HRID 2069876Notes

Reaction equation

HRID 2069876 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)C1C=CC=CC=1>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[CH:16]=1

Participants

3

Reactant 1

HCID 58150279HCID 58150279, compound

Product 1

HCID 125036743-(2-Hydroxyphenyl)pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-pyridyl)phenyl benzyl ether (6.67 g, 25.52 mmol) was dissolved in MeOH (100 mL). Argon was bubbled through this solution for 10 min to remove oxygen. Then Pd/C (350 mg 5 w %) was added, and the reaction mixture was put into the Parr-reactor and shaken for 16 hr under a hydrogen atmosphere at 80 psi. After the hydrogenation, the mixture was filtered over diatomaceous earth, and the colourless solution was evaporated to dryness. The crude product was recrystallized from 2-propanol to yield a white crystalline material (3.54 g, 79%). M.p.=185° C. 1H-NMR (CDCl3/MeOD):δ=8.76 (d, 1H), 8.43 (dd, 1H), 8.02 (dt, 1H), 7.39 (m, 1H), 7.21-7.29 (m, 2H), 6.95 (m, 2H).

Workup

  1. customArgon was bubbled through this solution for 10 min
  2. customto remove oxygen
  3. additionThen Pd/C (350 mg 5 w %) was added
  4. filtrationAfter the hydrogenation, the mixture was filtered over diatomaceous earth
  5. customthe colourless solution was evaporated to dryness
  6. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-5d41525cdaa648209b471074c6078691
Source dataset
uspto-grants-2012_10
Patent number
US08299202B2

Reaction notes

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