Hydrochloric Acid → HCID 14293622, compound

HRID 388264Notes

Reaction equation

HRID 388264 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:12][Si](C)(C)C)[C:10]#[N:11])=[CH:5][CH:4]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.O>[CH3:1][N:2]([CH3:17])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:12])[C:10]#[N:11])=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 11021259HCID 11021259, compound

Product 1

HCID 14293622HCID 14293622, compoundYield 102.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(dimethylamino)phenyl)-2-(trimethylsilyloxy)acetonitrile (7.19 g, 28.9 mmol) in THF (35 mL) was added 1 M aqueous HCl (1 mL) and the mixture was stirred for 1 hour. Additional 1 M HCl (1 mL) was then added and the reaction mixture was stirred for an additional 50 minutes. The mixture was made basic with solid NaHCO3 then diluted with EtOAc and water. The layers were separated and the organics were washed with saturated aqueous NaHCO3, water and brine. The solution was dried over Na2SO4 and concentrated in vacuo to give 2-(4-(dimethylamino)phenyl)-2-hydroxyacetonitrile as an off-white solid (5.2 g, quantitative yield). The product was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for an additional 50 minutes
  2. customThe layers were separated
  3. washthe organics were washed with saturated aqueous NaHCO3, water and brine
  4. dry with materialThe solution was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e850e4ed981d4106ab00ff5ca9f86cfa
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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