Trimethylsilyl cyanide → 3-Ethylamino-4-nitro-pyridine-2-carbonitrile

HRID 1594100Notes

Reaction equation

HRID 1594100 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.CN(C)NC(Cl)=O.[CH2:14]([NH:16][C:17]1[CH:18]=[N+:19]([O-])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[CH3:15]>CN(C=O)C.C(Cl)Cl.O>[CH2:14]([NH:16][C:17]1[C:18]([C:5]#[N:6])=[N:19][CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[CH3:15]

Participants

7

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 12343672N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amineHCID 22481940Dimethylaminocarbamoyl chloride

Product 1

HCID 223801443-Ethylamino-4-nitro-pyridine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

TMSCN (1.1 ml, 8.33 mmol) and dimethyl amino carbamoyl chloride (0.76 mL, 8.33 mmol.) are added to a solution of 3-ethylamino-4-nitro-pyridine-1-oxide (1 g, 6.94 mmol) in anhydrous DMF (10 mL) were added. The reaction mixture is stirred overnight at 80° C., cooled to room temperature, and diluted with CH2Cl2 and water. The combined organic layer is washed with water, brine, dried over Na2SO4, and concentrated. The residue is chromatographed eluting with 40% EtOAc-hexanes to afford 3-ethylamino-4-nitro-pyridine-2-carbonitrile as a yellow solid. 1H NMR (300 MHz, CD3OD): δ 7.82 (d, J=4.5 Hz, 1H), 7.50 (d, J=4.5 Hz, 1H), 3.70 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H)

Workup

  1. additionwere added
  2. temperaturecooled to room temperature
  3. washThe combined organic layer is washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is chromatographed
  7. washeluting with 40% EtOAc-hexanes

Sources & evidence

ORD record
ord-4da465e37d1241a291bb1738f205d2fd
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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