Serinol → 1,3-Propanediol, 2-[(6-methoxy-3-nitro-2-pyridinyl)amino]-
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](Cl)[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.[NH2:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16]>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Methoxy-2-chloro-3-nitropyridine (36.94 g, 195.9 mmol) and 2-aminopropane-1,3-diol (35.65 g, 391.3 mmol, 2 eq.) were stirred in ethanol (500 ml) at reflux under argon for 3 hours. The mixture was allowed to cool to room temperature and left overnight. The solvent was partially removed under reduced pressure (to ca. 150 ml) and the resulting bright yellow slurry was poured into ice-water (1.5 L) with vigorous stirring. The mixture was stirred for 1 hour then filtered with suction while cold. The solid was washed with ice-cold water (200 ml) and air-dried to give the title compound as a bright yellow solid (45.03 g, 94%). LCMS showed desired product (93%) plus 7% starting material. The product was used without further purification.