Sodium Hydroxide → 6-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylic acid

HRID 840308Notes

Reaction equation

HRID 840308 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[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+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22622486butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylate

Product 1

HCID 226225336-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylic acidYield 73.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylate (reference example 3) (0.36 g, 1.0 mmol) in THF (4 ml) and methanol (4 ml) was treated with aqueous sodium hydroxide 1N (4 ml) and allowed to stand at ambient temperature for 1.5 hours. The reaction was evaporated to a small volume, diluted with water and acidified with acetic acid. After standing for 18 hours, the precipitate was filtered, washed with water and ether, and dried (MgSO4) to give the title compound as a white solid (0.26 g, 71%).

Workup

  1. customThe reaction was evaporated to a small volume
  2. additiondiluted with water
  3. waitAfter standing for 18 hours
  4. filtrationthe precipitate was filtered
  5. washwashed with water and ether
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-9bedee97f00149a29fefeeaffd92bf53
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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