Ethanol → 5-Bromo-N-methyl-3-nitropyridin-2-amine

HRID 445621Notes

Reaction equation

HRID 445621 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[CH3:12][NH2:13].CCO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:13][CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 108681495-Bromo-N-methyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-chloro-3-nitropyridine (Matrix, Columbia, USA, 9.8 g, 41.3 mmol) in 250 ml THF was added 8 M methylamine in EtOH (Aldrich, Buchs, Switzerland, 12.9 ml, 103 mmol). The reaction mixture was stirred 1 h at rt then was quenched with 300 ml water. The precipite was filtered and the filtrate concentrated before being filtered again. The yellow solids were combined and dried to give the title compound as a yellow solid (HPLC: tR 3.13 min (Method A)).

Workup

  1. customthen was quenched with 300 ml water
  2. filtrationThe precipite was filtered
  3. concentrationthe filtrate concentrated
  4. filtrationbefore being filtered again
  5. customdried

Sources & evidence

ORD record
ord-a355d5361bce4509af81f3ec9290f393
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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