Dimethylformamide → N,N-dimethyl-5-nitropyridin-2-amine

HRID 2236153Notes

Reaction equation

HRID 2236153 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[H-].[Na+].[CH3:13][N:14](C=O)[CH3:15]>>[CH3:13][N:14]([CH3:15])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amine

Procedure

A mixture of 2-chloro-5-nitro-pyridine (500 mg, 3.15 mmol), in DMF (2 mL) was added dropwise to a suspension of NaH (151 mg, 6.31 mmol) in DMF (2 mL). The reaction mixture was stirred at room temperature for one hour then heated to 55° C. overnight. The reaction mixture was then poured into ice water, extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered and concentrated to give dimethyl-(5-nitro-pyridin-2-yl)-amine as a yellow solid. LCMS calcd for C7H11N3 (m/e) 137, obsd 138 (M+H).

Workup

  1. temperaturethen heated to 55° C. overnight
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d3051eb45e1246b78ad99a054f133bb1
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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