Water → 4-Nitropicolinamide
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
Product 1
Reagents, catalysts & solvents 1
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
- washwashed with NaHCO3, brine
- dry with materialdried over Na2SO4
- 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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