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

HRID 1870739
Notes
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Reaction equation

HRID 1870739 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028Tetrahydrofuran
Solvent

Procedure

A solution of butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylate (reference example 11) (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 air dried 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, and air
  6. customdried

Sources & evidence

ORD record
ord-2c3bf1ec83ef4b888d5e2acb7232c7f5
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06100258

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes