Pyridine → HCID 11171405, compound

HRID 232085

Reaction equation

HRID 232085 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 11171405HCID 11171405, compound

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-a88393f3ca6d4715b4dc0b02d1da9f73
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Linked notes

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