Water → 4-Nitropicolinamide

HRID 1515571Notes

Reaction equation

HRID 1515571 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]#[N:11])[CH:5]=1)([O-:3])=[O:2].Cl[Si](C)(C)C.[OH2:17]>CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH2:11])=[O:17])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 5686504-Nitropicolinonitrile

Product 1

HCID 103971654-NitropicolinamideYield 119.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Nitropicolinonitrile (100 mg, 0.67 mmol), chlorotrimethylsilane (0.17 mL, 1.4 mmol) and H2O (0.024 mL, 1.4 mmol) was sonicated in a sonicator at rt for 1.0 h. It was diluted with EtOAc, washed with NaHCO3, brine and dried over Na2SO4. After removal of solvent, 99A (134 mg, 100% yield) was obtained as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 8.29 (dd, J=5.27, 2.20 Hz, 1H) 8.74 (d, J=2.20 Hz, 1H) 8.98 (d, J=5.27 Hz, 1H).

Workup

  1. washwashed with NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customAfter removal of solvent

Sources & evidence

ORD record
ord-a8dc18ddd7ed40a49d1b140a034aa5a0
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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