Potassium Carbonate → HCID 58476611, compound

HRID 2388011Notes

Reaction equation

HRID 2388011 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]#[C:12][Si](C)(C)C)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:11]([C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([CH3:1])=[N:3][CH:4]=1)#[CH:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59404985HCID 59404985, compound

Product 1

HCID 58476611HCID 58476611, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methyl-3-nitro-5-[(trimethylsilyl)ethynyl]pyridine (2.32 g, 9.90 mmol) in methanol (22 mL) was cooled to 0° C. and potassium carbonate (137 mg, 0.99 mmol) was added. The reaction mixture was allowed to warm and stir at rt for 10 min, during which time a yellow precipitate formed. The reaction mixture was then concentrated and diluted with ether (200 mL). The organic solution was washed with water (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated to give 5-ethynyl-2-methyl-3-nitropyridine (1.48 g, 92%) as a solid. LCMS (FA): Rt=1.64 min, m/z=163.0 (M+H).

Workup

  1. temperatureto warm
  2. customformed
  3. concentrationThe reaction mixture was then concentrated
  4. additiondiluted with ether (200 mL)
  5. washThe organic solution was washed with water (200 mL) and brine (200 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-92d8e47b938d4b0889d286f3e868e977
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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