Sodium Hydroxide → 6-[N-(5-Bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic Acid

HRID 840288Notes

Reaction equation

HRID 840288 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([O:19]CCCC)=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].[OH-].[Na+].C(OCC)C.CCCCCC>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][CH:27]([CH3:28])[CH3:29])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21584099Diethylether hexaneHCID 22622534Butyl 6-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate

Product 1

HCID 226225576-[N-(5-Bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic AcidYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Butyl 6-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate (reference example 10) (0.22 g, 0.47 mmol) in THF (3 ml) and methanol (3 ml) was treated with a 1N solution of aqueous sodium hydroxide (3 ml) and left at ambient temperature for 1.5 hours (after which time TLC (1:1 diethyl ether/hexane) indicated that none of the ester remained). The reaction mixture was evaporated to low bulk, taken up in a little water and acidified with acetic acid to produce a gum. The gum did not solidify so it was extracted with ethyl acetate (×2) and the combined extracts washed with brine, dried (MgSO4) and evaporated to give a gum. The gum was evaporated from toluene and dichloromethane to give the title compound as a foam (140mg, 73%).

Workup

  1. customThe reaction mixture was evaporated to low bulk
  2. customto produce a gum
  3. extractionwas extracted with ethyl acetate (×2)
  4. washthe combined extracts washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a gum
  8. customThe gum was evaporated from toluene and dichloromethane

Sources & evidence

ORD record
ord-ea60a8f29cab4d27bceb746ccfe4d812
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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