2-Amino-2-methyl-1-propanol → HCID 64538625, compound

HRID 855858Notes

Reaction equation

HRID 855858 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][N:11]=1>CN(C=O)C.O>[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][O:4][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 64538625HCID 64538625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-amino-2-methyl-1-propanol (0.5 ml, 5.60 mmol), in DMF (20 mL) was added NaH 60% (0.67 g, 16.80 mmol) and then 6-chloronicotinonitrile (2.03 g, 11.22 mmol). The mixture heated to 70° C. for 2 hours and then stirred at room temperature overnight. The reaction mixture was taken up in H2O and extracted with EtOAc. The organic phase was washed with water (3×), dried over Na2SO4 and concentrated under reduced pressure to provide the titled compound as a pale yellow solid. MS (DCI) m/z 235 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-707e718169764e75bf946824182e098f
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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