Acetic Acid → 3-Chloro-2-(4-nitrophenylazo)-5-hydroxypyridine

HRID 367072Notes

Reaction equation

HRID 367072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[OH-].[K+].F[B-](F)(F)F.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]#[N:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(O)(=O)C>O>[Cl:1][C:2]1[C:7]([N:26]=[N:25][C:22]2[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=2)=[N:6][CH:5]=[C:4]([OH:8])[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 680064-Nitrobenzenediazonium tetrafluoroborateHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 1358333213-Chloro-2-(4-nitrophenylazo)-5-hydroxypyridineYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-chloro-3-pyridinol (20.0 g, 0.154 mol, Aldrich) and KOH (13.0 g, 0.232 mol) in 300 mL of water at 0° C. was added p-nitrobenzenediazonium tetrafluoroborate (36.6 g, 0.154 mol, Aldrich). After 1 hour, 50 mL of glacial acetic acid was added, and the bright red precipitate was filtered and air-dried. Chromatography (silica gel; CH2Cl2 /MeOH, 95:5-90:10) afforded the title compound as a bright red solid (28.8 g, 67%): 1H NMR (DMSO-d6, 300 MHz) δ 7.14 (d, J=2.4 Hz, 1H), 7.89 (d, J=2.4 Hz, 1H), 8.00 (m, 2H), 8.39 (m, 2H); MS (CI/NH3) m/z: 279, 281 (M+H)+.

Workup

  1. filtrationthe bright red precipitate was filtered
  2. customair-dried

Sources & evidence

ORD record
ord-7e033426576d4e99af370137ff4bfada
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

Loading…