Pyridine → (2-(Pyridin-2-yl)phenyl)methanol

HRID 1199447Notes

Reaction equation

HRID 1199447 reaction equation
N[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N([O-])=O.[Na+].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>Cl.O>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 214392-Aminobenzyl alcoholHCID 23668193Sodium Nitrite

Product 1

HCID 11171405(2-(Pyridin-2-yl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

2-Aminobenzylalcohol (10 g) was dissolved in concentrated hydrochloric acid (25 ml) and the solution diluted with water (20 ml). The solution was stirred at 0° and a solution of sodium nitrite (5.9 g) in water (20 ml) added dropwise. The mixture was stirred at 0° for 40 minutes. The solution was added dropwise to pyridine (92 ml) stirred at 80°. After stirring at 80° for 90 minutes the mixture was concentrated in vacuo and the residue heated with 880 ammonia (100 ml). The mixture was concentrated in vacuo and the residue slurried with water and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried and evaporated. Flash chromatography produced the sub-title compound as a red oil (3.8 g). M.S. m/e 185 Base Peak 80.

Workup

  1. stirringThe mixture was stirred at 0° for 40 minutes
  2. stirringstirred at 80°
  3. stirringAfter stirring at 80° for 90 minutes the mixture
  4. concentrationwas concentrated in vacuo
  5. temperaturethe residue heated with 880 ammonia (100 ml)
  6. concentrationThe mixture was concentrated in vacuo
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate was washed with brine
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-cfd01c32270e4625aed937289ce96a31
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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