Diethyl Ether → 6-[N-(5-Bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]([Cl:29])=[CH2:28])=[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].C1COCC1.[OH-].[Na+].CCOCC>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]([Cl:29])=[CH2:28])=[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 4
Product 1
Reagents, catalysts & solvents 1
Procedure
n-Butyl 6-[N-(5-bromo-2-(2-chloroprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate (0.24 g, 0.5 mmol) was dissolved in methanol (2 ml), THF (2 ml) and treated with aqueous 1N sodium hydroxide solution (2 ml). The resultant solution was left at ambient temperature for 1.5 hours, evaporated to low bulk and the resultant precipitate dissolved in water and acidified with acetic acid to give a gummy precipitate. It was extracted with methylene chloride and the organic extracts dried and evaporated to give a gum. Trituration with ether yielded a solid which was filtered and sucked dry to give the title compound as a white solid (0.16 g, 75%).
Workup
- customevaporated to low bulk
- dissolutionthe resultant precipitate dissolved in water
- customto give a gummy precipitate
- extractionIt was extracted with methylene chloride
- customthe organic extracts dried
- customevaporated
- customto give a gum
- filtrationwas filtered
- customsucked dry
Sources & evidence
- ORD record
- ord-4b9fd878aa0c47c684c3f54a1249a7cf
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06100258
Reaction notes
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