Sodium Hydroxide → HCID 86625533, compound

HRID 2266019Notes

Reaction equation

HRID 2266019 reaction equation
[CH3:1][O:2][N:3]([CH3:22])[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=1[C:15]#[C:16][Si](C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[C:15]([C:6]1[N:7]=[C:8]([C:11]([F:14])([F:12])[F:13])[CH:9]=[CH:10][C:5]=1[C:4]([N:3]([O:2][CH3:1])[CH3:22])=[O:21])#[CH:16]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59598308HCID 59598308, compound

Product 1

HCID 86625533HCID 86625533, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-methoxy-N-methyl-6-trifluoromethyl-2-trimethylsilanylethynyl-nicotinamide (148 g, 0.449 mmol) in THF (1 ml) and CH3OH (0.5 ml) was added a solution of 1N-NaOH (0.5 ml) and the mixture was stirred for 50 min at room temperature. The resulting residue was dissolved in H2O and then washed three times with EtOAc, acidified with 1N HCl to pH 1˜2. The solution was extracted three times with methylene chloride and then dried over anhyd. Na2SO4 and concentrated in vacuo to give 2-ethynyl-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (116 mg, 99%).

Workup

  1. washwashed three times with EtOAc
  2. extractionThe solution was extracted three times with methylene chloride
  3. customdried over anhyd
  4. concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-934c4cdfece14bee89600d4f1eb13796
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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