Ethanol → 6-(N-[5-Bromo-2-propoxybenzyl]-N-ethylamino)pyridazine-3-carboxylic Acid

HRID 840291Notes

Reaction equation

HRID 840291 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15]C(C#N)=[CH:13][CH:12]=1)[CH2:9][CH3:10].[OH-:24].[Na+].[CH2:26]([OH:28])[CH3:27]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:19]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:27]([C:26]([OH:24])=[O:28])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 226225206-[N-(5-Bromo-2-propoxybenzyl)-N-ethylamino]-3-cyanopyridazine

Product 1

HCID 226225306-(N-[5-Bromo-2-propoxybenzyl]-N-ethylamino)pyridazine-3-carboxylic AcidYield 79%

Conditions

Temperature
70 °C

Procedure

6-[N-(5-Bromo-2-propoxybenzyl)-N-ethylamino]-3-cyanopyridazine (reference example 18) (1.5 g, 4 mmol) in ethanol (100 ml) was treated with aqueous sodium hydroxide (20 ml, 2M, 40 mmol) and was heated to 70° C. for 16 hours. The solvents were evaporated at reduced pressure, the residue dissolved in water, acidified with acetic acid and extracted with ethyl acetate (×4). The combined organic phases were washed with water and brine dried over MgSO4 and concentrated in vacuo. The resulting gum was triturated with ether to give the title compound as a solid (1.24 g, 79%).

Workup

  1. customThe solvents were evaporated at reduced pressure
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate (×4)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting gum was triturated with ether

Sources & evidence

ORD record
ord-1b95f1893472463fb58928ccf141c474
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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