Water → 6-CHLORO-N-ETHYL-3-NITROPYRIDIN-2-AMINE

HRID 2229304Notes

Reaction equation

[CH2:1]([NH2:3])[CH3:2].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[N:6]=1.O.CCOC(C)=O>C1(C)C=CC=CC=1>[Cl:14][C:7]1[N:6]=[C:5]([NH:3][CH2:1][CH3:2])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

An ice-cold solution of EtNH2 (49.8 g, 1.10 mol) in toluene (200 mL) was added over 15 min to an ice-cold solution of 2,6-dichloro-3-nitropyridine (100.0 g, 0.52 mol) in toluene (225 mL). The mixture was stirred at 0° C. for 45 min. Water (500 mL) and EtOAc (500 mL) were added and the phases were separated. The organic layer was successively washed with water (200 mL) and brine (200 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residual solid was recrystallised from MeOH to give the title compound (83.7 g, 80% yield) as yellow needles.

Workup

customthe phases were separated
washThe organic layer was successively washed with water (200 mL) and brine (200 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residual solid was recrystallised from MeOH

Sources & evidence

ORD record: ord-b7a259db5f014ce68be845f972306556
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420359B1

Reaction notes

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