Hydroxylamine → HCID 15287762, compound
Reaction equation
[NH2:1][OH:2].[C:3]([O:12][CH2:13][CH3:14])(=[O:11])/[CH:4]=[CH:5]\[C:6]([O:8][CH2:9][CH3:10])=[O:7]>>[OH:2][NH:1][C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][C:3]([O:12][CH2:13][CH3:14])=[O:11]Participants
3
Procedure
Hydroxylamine free base (50% aqueous solution, 2.0 g, 30.3 mmol) is added dropwise to diethyl maleate (4.41 g, 25.6 mmol) and stirred for 60 minutes to give diethyl N-hydroxyaspartate. Toluene (25.02 g) and p-toluenesulfonic acid (0.05 g, 0.26 mmol) are added to the reaction mixture and refluxed for 4.5 hours to afford diethyl 2-aminomaleate. The reaction mixture is cooled to room temperature and added acetic acid (7.0 g) and 2-ethylacrolein (2.13 g, 25, 0 mmol). The reaction mixture is stirred at 80°-90° C. for 24 hours. It is concentrated under reduced pressure and analyzed by GLC using an external standard. The analysis showed the yield of diethyl 5-ethylpyridine-2,3-dicarboxylate is about 35%.
Sources & evidence
- ORD record
- ord-db05f582488c4c34948caa850b87e3b0
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05808067
Reaction notes
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