Potassium Hydroxide → 3-Bromo-2-(4-nitrophenylazo)-5-hydroxypyridine

HRID 2185732Notes

Reaction equation

HRID 2185732 reaction equation
[Br: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]>O.C(O)(=O)C>[Br: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 3

HCID 14797Potassium HydroxideHCID 680064-Nitrobenzenediazonium tetrafluoroborateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 1356101333-Bromo-2-(4-nitrophenylazo)-5-hydroxypyridineYield 33,735.398%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

5-Bromo-3-pyridinol from Example 12b (8.7 g, 0.050 mmol) and KOH (1.1 g, 19.6 mmol) were dissolved in water (200 mL). A suspension of p-nitrobenzenediazonium tetrafluoroborate (11.8 g, 0.50 mol, prepared as described in J. Org. Chem., 44: 1572-15783 (1979)) was added. The reaction was stirred for 1 hour, diluted with acetic acid (50 mL) and filtered. The crude product was allowed to air dry, then chromatographed (silica gel; chloroform/methanol, 95:5-90:10) to provide the title compound (5.45 g, 34% yield): MS (CI/NH3) m/z 323, 325 (M+H)+; NMR (DMSO-d6, 300 MHz) δ8.48-8.43 (m, 2H), 8.21 (d, J=2.4 Hz, 1H), 8.09-8.06 (m, 2H), 7.72 (d, J=2.4 Hz, 1H).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. customto air dry
  4. customchromatographed (silica gel; chloroform/methanol, 95:5-90:10)

Sources & evidence

ORD record
ord-bf51b629f4294c109141b3e037a2993a
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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