1,2-Dichlorobenzene → HCID 178424441, compound

HRID 1039549Notes

Reaction equation

HRID 1039549 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=2[OH:11])[CH2:3][CH2:2]1.ClC1C=CC=CC=1Cl.CC(C)([O-])C.[K+].[OH:26][C:27]1[CH:32]=[C:31]([Cl:33])[N:30]=[N:29][C:28]=1Cl>C(O)(C)(C)C>[Cl:33][C:31]1[N:30]=[N:29][C:28]([O:11][C:5]2[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:1]2[CH2:3][CH2:2]2)=[C:27]([OH:26])[CH:32]=1

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 229399512-Cyclopropyl-6-methylphenolHCID 23665647Potassium tert-butoxideHCID 178516198HCID 178516198, compound

Product 1

HCID 178424441HCID 178424441, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a mixture of 1.34 g (9.05 mmol) of 2-cyclopropyl-6-methylphenol and 1,2-dichlorobenzene (7.00 mL) was added 1.20 g (9.05 mmol) of 85% potassium t-butoxide at room temperature. The resultant mixture was heated to 180° C. and subjected to azeotropic dehydration under reflux while stirring for 30 minutes. To the resultant solution was added dropwise the preliminarily prepared solution of 4.97 g (purity: 96.0%; 2.89 mmol) of 4-hydroxy-3,6-dichloropyridazine in t-butanol (35.0 g) at 170° C. over 2 hours. (The t-butanol was distilled off simultaneously with the dropwise addition of the solution.) After stirring at 180° C. for another 2 hours, the 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 701 mg of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 88%) and 6.9 mg of 3-chloro-6-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 0.9%) were obtained.

Workup

  1. temperatureunder reflux
  2. distillation(The t-butanol was distilled off simultaneously with the dropwise addition of the solution
  3. stirring) After stirring at 180° C. for another 2 hours
  4. additiona 1 N aqueous hydrochloric acid solution and methanol were added to the reaction mixture
  5. customto obtain a uniform solution

Sources & evidence

ORD record
ord-c68d10164fe945278c1c370d21ceb03f
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

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