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

HRID 1604355Notes

Reaction equation

HRID 1604355 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 .paren open-st.MgSO4 .paren close-st.- and evaporated to give a gum. The gum was evaporated from toluene and dichloromethane to give the title compound as a foam (140 mg 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. customdried
  6. customMgSO4 .paren close-st
  7. custom- and evaporated
  8. customto give a gum
  9. customThe gum was evaporated from toluene and dichloromethane

Sources & evidence

ORD record
ord-bf1231a890c14f279d99e87cbe82220d
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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