2-(Dimethylamino)ethanol → HCID 12566181, compound

HRID 1632166Notes

Reaction equation

HRID 1632166 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[CH:14][CH:13]=[CH:12][N:11]=1>CN(C=O)C>[ClH:9].[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:10]1[C:15]([C:16]#[N:17])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 810792-Chloronicotinonitrile

Product 1

HCID 12566181HCID 12566181, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To 2-dimethylaminoethanol (1.3 g, o., 015 m) in DMF (25 mL) was added 57% NaH in mineral oil (0.63 g, 0.015 m). After stirring 0.5 hours at 25° C., a solution of 2-chloro-3-cyanopyridine (2 g, 0.015 m) in DMF (10 mL) was added. The reaction mixture was stirred 20 hours, concentrated to 10 mL and added to H2O (25 mL). The solution was extracted with CHCl3 ; the organic layer was dried, filtered and concentrated. The resulting oil was dissolved in Et2O and treated with HCl in MeOH to yield after recrystallization from Et2O-iso-PrOH 0.8 g (23%) of (XI) m.p. 148°-150° C.

Workup

  1. stirringThe reaction mixture was stirred 20 hours
  2. concentrationconcentrated to 10 mL
  3. additionadded to H2O (25 mL)
  4. extractionThe solution was extracted with CHCl3
  5. customthe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe resulting oil was dissolved in Et2O
  9. additiontreated with HCl in MeOH
  10. customto yield
  11. customafter recrystallization from Et2O-iso-PrOH 0.8 g (23%) of (XI) m.p. 148°-150° C.

Sources & evidence

ORD record
ord-651471c0b9c947f2bb8cda4a4c659d79
Source dataset
uspto-grants-1984_10
Patent number
US04474781

Reaction notes

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