Hydrochloric Acid → HCID 178424441, compound

HRID 1039554Notes

Reaction equation

HRID 1039554 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1Cl.[CH:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[OH:20])[CH2:12][CH2:11]1.[OH-].[K+].Cl>CO.C(O)CCCCCCC>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:20][C:14]2[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:13]=2[CH:10]2[CH2:11][CH2:12]2)=[C:2]([OH:1])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 229399512-Cyclopropyl-6-methylphenolHCID 178516198HCID 178516198, compound

Product 1

HCID 178424441HCID 178424441, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9571-OctanolSolvent

Procedure

To a mixture of 307 mg (purity: 98.0%; 1.82 mmol) of 4-hydroxy-3,6-dichloropyridazine and 833 mg (5.57 mmol) of 2-cyclopropyl-6-methylphenol were added 1-octanol (3.36 mL) and 324 mg (5.50 mmol) of 95% potassium hydroxide at room temperature. The resultant mixture was heated to 180° C. while stirring, and stirred at that temperature for 4 hours. Then, the resultant reaction mixture was cooled to room temperature, and a 1 N aqueous hydrochloric acid solution and methanol were added to the reaction mixture to obtain a uniform solution. The obtained solution was quantitatively determined by an HPLC internal standard analysis method, which showed that 113 mg of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 23%) and 1.4 mg of 3-chloro-6-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 0.3%) were obtained.

Workup

  1. stirringstirred at that temperature for 4 hours
  2. customThen, the resultant reaction mixture
  3. customto obtain a uniform solution

Sources & evidence

ORD record
ord-f0aa9eb54a004cc792415854b0d61638
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

Loading…