Dimethylformamide → HCID 86657560, compound

HRID 1422838Notes

Reaction equation

HRID 1422838 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1.CC(C)([O-])C.[K+].[Cl:23][C:24]1[N:25]=[N:26][C:27](Cl)=[CH:28][CH:29]=1>O>[CH3:6][O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:27]2[N:26]=[N:25][C:24]([Cl:23])=[CH:29][CH:28]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 673313,6-DichloropyridazineHCID 88068Methyl 3-HydroxybenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86657560HCID 86657560, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide (8.0 mL) solution of 3-hydroxy-benzoic acid methyl ester (928 mg, 6.1 mmol) was added potassium t-butoxide (750 mg, 6.7 mmol). Upon stirring the reaction at room temperature for 15 min, 3,6-dichloro-pyridazine (1.0 g, 6.7 mmol) was added. The reaction was stirred at room temperature for 15 h. Crude reaction mass was added to water, aqueous layer was acidified to pH 4.0 and product was extracted with ethyl acetate to give 3-(6-chloro-pyridazin-3-yloxy)-benzoic acid methyl ester (950 mg).

Workup

  1. customthe reaction at room temperature for 15 min
  2. stirringThe reaction was stirred at room temperature for 15 h
  3. customCrude reaction mass
  4. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-dcea6fadb8bc4325a73e1a65d5215162
Source dataset
uspto-grants-2015_01
Patent number
US08927549B2

Reaction notes

Loading…