Ethanol → Ethyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylite

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([OH:19])=O)=[CH:13][CH:12]=1)[CH2:9][CH3:10].S(=O)(=O)(O)O.[CH2:27](O)[CH3:28]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([CH2:17][O:19][CH2:27][CH3:28])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

Reactant 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

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

Product 1

HCID 18693265Ethyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylite

Procedure

The 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxylic acid (example 8) (6.5 g) was suspended in ethanol (30 ml) and treated cautiously with concentrated sulphuric acid (1.5 ml). The reaction was heated to reflux overnight, then the organic solvent was evaporated. The residue was partitioned between ethyl acetate/water and the organic phase was dried over (MgSO4) and evaporated to give the title compound as a brown solid (5.86 g).