Dimethylformamide → 5-(Pyridin-2-ylamino)pentanenitrile

HRID 585545Notes

Reaction equation

HRID 585545 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[K+].Br[CH2:11][CH2:12][CH2:13][C:14]#[N:15].[CH3:16]N(C=O)C>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:16][CH2:11][CH2:12][CH2:13][C:14]#[N:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 104392-AminopyridineHCID 214124-BromobutyronitrileHCID 82127Potassium hydride

Product 1

HCID 219279325-(Pyridin-2-ylamino)pentanenitrile

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-aminopyridine (8.7 g, Aldrich) in DMF (75 mL) was added potassium hydride (12.6 g, 30 wt. % dispersion in mineral oil, Aldrich). After 1 hr, 4-bromobutyronitrile (15 g, Aldrich) was added. The mixture was heated to 60° C. for 16 hr. The mixture was quenched with water and the volatiles were removed in vacuo. The residue was extracted with ethyl acetate. The extract was filtered through a bed of silica gel and distilled in vacuo. The fraction boiling at 150° C. to 170° C. was collected to provide the title product as a white solid. 1H (CDCl3) δ 1.78 (4H, m); 2.41 (2H, t); 3.36 (2H, q); 4.53 (2H, broad t); 6.38 (1H, dt); 6.57 (1H, ddd); 7.42 (1H, ddd); 8.08 (1H, ddd). Step 2 (Alternate Procedure to Step 3, EXAMPLE A)

Workup

  1. customThe mixture was quenched with water
  2. customthe volatiles were removed in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. filtrationThe extract was filtered through a bed of silica gel
  5. distillationdistilled in vacuo
  6. customThe fraction boiling at 150° C. to 170° C. was collected

Sources & evidence

ORD record
ord-590a20a4d36f49a9b6db5ae39f0127d3
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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