Potassium Hydroxide → 5-Bromo-6-cyclobutoxynicotinic acid

HRID 1025991Notes

Reaction equation

HRID 1025991 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH:12]1([OH:16])[CH2:15][CH2:14][CH2:13]1.[OH-].[K+]>CS(C)=O.O>[Br:1][C:2]1[C:3]([O:16][CH:12]2[CH2:15][CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 76218CyclobutanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 666788435-Bromo-6-cyclobutoxynicotinic acidYield 82%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

5-Bromo-6-chloronicotinic acid (CAN 29241-62-1, 2.0 g, 8.46 mmol) was dissolved in DMSO (20.0 mL). Cyclobutanol (793 mg, 857 μL, 11.0 mmol) and potassium hydroxide powder (1.42 g, 25.4 mmol) were added and the mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was acidified (under ice-water bath cooling) with 37% HCL in water (pH=2). The suspension was filtered, washed with water and the solid was dried to yield 1.88 g (82%) of the title compound as a white solid; MS (ESI): 270.2 (M−H)−.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water
  3. customthe solid was dried

Sources & evidence

ORD record
ord-003b545a9b614c16bac6c058142b6baa
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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