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

HRID 1243508Notes

Reaction equation

HRID 1243508 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 meneral 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).

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-fec92bf872324cc1ab4b698216380f2d
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

Loading…