Sodium hydride → 6-(2-Methylpyridin-3-yloxy)pyridazine-3-carboxylic acid ethyl ester

HRID 840550

Reaction equation

HRID 840550 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]([CH3:10])=[N:6][CH:7]=[CH:8][CH:9]=1.[CH2:11]([O:13][C:14]([C:16]1[N:17]=[N:18][C:19](Cl)=[CH:20][CH:21]=1)=[O:15])[CH3:12]>CN(C=O)C>[CH2:11]([O:13][C:14]([C:16]1[N:17]=[N:18][C:19]([O:3][C:4]2[C:5]([CH3:10])=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:20][CH:21]=1)=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707192-Methylpyridin-3-olHCID 10352425Ethyl 6-chloropyridazine-3-carboxylate

Product 1

HCID 544471436-(2-Methylpyridin-3-yloxy)pyridazine-3-carboxylic acid ethyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.21 g of an 80% dispersion in oil, 7.0 mmol) was added to a solution of 3-hydroxy-2-methylpyridine (0.88 g, 8.0 mmol) in DMF (15 ml). After 1.5 h at r.t. a solution of 6-chloropyridazine-3-carboxylic acid ethyl ester (Chem. Pharm. Bull. 1994, 42(2), 371) (1.0 g, 5.4 mmol) in DMF (10 ml) was added and the mixture was stirred for a further 1.5 h. The DMF was removed in vacuo and the residue partitioned between dil. aq. NaOH (50 ml) and CH2Cl2 (100 ml). After drying (Na2SO4) the organics were evaporated to give the title compound as an off-white solid (1.09 g, 78%).

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue partitioned between dil. aq. NaOH (50 ml) and CH2Cl2 (100 ml)
  3. dry with materialAfter drying (Na2SO4) the
  4. customorganics were evaporated

Sources & evidence

ORD record
ord-694340372c0f4998a5679fd0a7b14521
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Linked notes

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