Hydrochloric Acid → HCID 66678843, compound

HRID 240693Notes

Reaction equation

HRID 240693 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[CH:12]1([OH:16])[CH2:15][CH2:14][CH2:13]1.[OH-].[K+].Cl>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[CH:5]=[N:6][C:7]=1[O:16][CH:12]1[CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 76218CyclobutanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 66678843HCID 66678843, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

5-Bromo-6-chloro-3-pyridinecarboxylic 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-fa5857f54a7c4de1ac258a4b1100bb43
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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