Dimethylamine → 5-Bromo-N,N-dimethyl-3-nitropyridin-2-amine

HRID 241065Notes

Reaction equation

HRID 241065 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][NH:13][CH3:14]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:13]([CH3:14])[CH3:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 260763465-Bromo-N,N-dimethyl-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-chloro-3-nitropyridine (J. Heterocyclic Chem. 2003, 40, 261) (128 mg, 0.54 mmol) was taken into THF (0.25 mL) followed by addition of 40 W % aqueous dimethylamine (0.25 mL) and the resulting solution was stirred for 1 h at room temperature. The mixture was then partitioned with ethyl ether and 1 M aqueous hydrochloric acid. The organic solution was then washed with additional 1 M aqueous hydrochloric acid (3×) then dried over magnesium sulfate, filtered and concentrated to give 5-bromo-N,N-dimethyl-3-nitropyridin-2-amine. MS (EI) for C7H8N3O2Br: 246, 248 (MH+, Br pattern).

Workup

  1. customThe mixture was then partitioned with ethyl ether and 1 M aqueous hydrochloric acid
  2. washThe organic solution was then washed with additional 1 M aqueous hydrochloric acid (3×)
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b79480e94cb64373bd9217576bd72068
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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