Hydrochloric Acid → HCID 178424440, compound

HRID 2424327Notes

Reaction equation

HRID 2424327 reaction equation
[Br:1]N1C(=O)CCC1=O.CN(C)C=O.[Cl:14][C:15]1[N:20]=[N:19][C:18]([O:21][C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH:29]2[CH2:31][CH2:30]2)=[C:17]([OH:32])[CH:16]=1.Cl>O>[Br:1][C:16]1[C:17]([OH:32])=[C:18]([O:21][C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH:29]2[CH2:31][CH2:30]2)[N:19]=[N:20][C:15]=1[Cl:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 178424441HCID 178424441, compound

Product 1

HCID 178424440HCID 178424440, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

108 mg (0.607 mmol) of N-bromosuccinimide was added to a N,N-dimethylformamide (2 mL) solution containing 157 mg (0.567 mmol) of 6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-4-pyridazinol, and the resulting mixture was stirred at room temperature for 3 hours and 30 minutes. Water, and then, 4 mol/L hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by preparative thin-layer chromatography (available from MERCK CO. 1.05744, developed by hexane:ethyl acetate=2:1) to obtain 123 mg (0.346 mmol, Yield: 61.0%) of 5-bromo-6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (Compound No. 3843).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by preparative thin-layer chromatography (available from MERCK CO. 1.05744, developed by hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d652078102024cbe9c437c25ed2983f5
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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