Hydrochloric Acid → HCID 66678843, compound

HRID 240748Notes

Reaction equation

HRID 240748 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].[OH-].[K+].[CH:14]1([OH:18])[CH2:17][CH2:16][CH2:15]1.Cl>O.CS(C)=O>[Br:1][C:2]1[C:3]([O:18][CH:14]2[CH2:17][CH2:16][CH2:15]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

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

Product 1

HCID 66678843HCID 66678843, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

In a 250 mL pear-shaped flask, 5-bromo-6-chloronicotinic acid (5 g, 21.1 mmol, Eq: 1.00) was combined with DMSO (75 mL) to give a colorless solution. Potassium hydroxide (3.56 g, 63.4 mmol, Eq: 3) powdered and cyclobutanol (1.98 g, 2.15 ml, 27.5 mmol, Eq: 1.3) were added and the reaction mixture was stirred at RT overnight (->yellow solution). TLC indicated the reaction to be complete. The mixture was diluted with 75 ml H2O, cooled to 0-5° C., and neutralized with 8 ml 25% HCl (slowly added dropwise under stirring whereupon a white solid formed). The solid was filtered off, washed with 2×20 mL H2O and dried overnight on HV; thereby, 5.26 g of 5-bromo-6-cyclobutoxy-nicotinic acid was obtained as white solid; MS (EI) 272.2, 274.2 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customthe reaction
  3. temperaturecooled to 0-5° C.
  4. additionslowly added dropwise
  5. stirringunder stirring whereupon a white solid
  6. customformed)
  7. filtrationThe solid was filtered off
  8. washwashed with 2×20 mL H2O
  9. customdried overnight on HV

Sources & evidence

ORD record
ord-dfcc77cc0f0348949f7706e1eef90c5c
Source dataset
uspto-grants-2014_02
Patent number
US08648099B2

Reaction notes

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