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
4
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).
Workup
- temperatureThe reaction was heated
- temperatureto reflux overnight
- customthe organic solvent was evaporated
- customThe residue was partitioned between ethyl acetate/water
- dry with materialthe organic phase was dried over (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-10af7cfa1ce14d31bb4a8550cf7c0de1
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06100258
Reaction notes
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