2,6-Bis(3-pyridyl)phenyl benzyl ether → HCID 46316636, compound

HRID 2069875Notes

Reaction equation

HRID 2069875 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)C1C=CC=CC=1>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[C:9]=2[OH:8])[CH:16]=1

Participants

3

Reactant 1

HCID 581502802,6-Bis(3-pyridyl)phenyl benzyl ether

Product 1

HCID 46316636HCID 46316636, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-Bis(3-pyridyl)phenyl benzyl ether (16.70 g, 49.35 mmol) was dissolved in MeOH (200 mL). Argon was bubbled through this solution for 10 min to remove oxygen. Then Pd/C (500 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 resulting precipitate was redissolved by heating to reflux. The hot mixture was filtered over diatomaceous earth, and the filter cake thoroughly washed with hot MeOH. Upon cooling to room temperature, the product crystallized as a white crystalline material (12.25 g, 99%). M.p.=211° C. 1H-NMR (DMSO):δ=8.74 (d, 2H), 8.55 (dd, 2H), 7.95 (dt, 2H), 7.48 (m, 2H), 7.34 (d, 2H), 7.11 (t, 1H).

Workup

  1. customArgon was bubbled through this solution for 10 min
  2. customto remove oxygen
  3. additionThen Pd/C (500 mg 5 w %) was added
  4. dissolutionAfter the hydrogenation, the resulting precipitate was redissolved
  5. temperatureby heating to reflux
  6. filtrationThe hot mixture was filtered over diatomaceous earth
  7. washthe filter cake thoroughly washed with hot MeOH
  8. customthe product crystallized as a white crystalline material (12.25 g, 99%)

Sources & evidence

ORD record
ord-783196c1fcc94f86baade4a0b860590d
Source dataset
uspto-grants-2012_10
Patent number
US08299202B2

Reaction notes

Loading…