Hydrochloric Acid → HCID 66678843, compound

HRID 1958192Notes

Reaction equation

HRID 1958192 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+].Cl>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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 76218Cyclobutanol2×HCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 66678843HCID 66678843, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

5-Bromo-6-chloronicotinic acid (CAN 29241-62-1; 3 g, 12.7 mmol) was dissolved in DMSO (30 mL); cyclobutanol (1.19 g, 1.29 ml, 16.5 mmol) and potassium hydroxide (powder) (2.14 g, 38.1 mmol) were added and the reaction mixture was stirred at room temperature for 5 h. More cyclobutanol (0.5 mL) and KOH (1 g) was added and the reaction mixture was stirred at room temperature for another 2 days. Water (30 mL) was added and the mixture was acidified (cooling) with 5 mL 37% HCl in water (pH=2). The suspension was filtered and washed with water. The cake was dried in vacuo to obtain the title compound (3.1 g, 88.7%) as white solid; MS (ESI) 270.2 (M−H)−.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for another 2 days
  2. filtrationThe suspension was filtered
  3. washwashed with water
  4. customThe cake was dried in vacuo

Sources & evidence

ORD record
ord-41e115c7af1a4d42b66f79c112af77ef
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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