Ethyl chloroacetate → HCID 59547216, compound

HRID 1097213Notes

Reaction equation

HRID 1097213 reaction equation
[Se-2:1].[Na+].[Na+].Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[CH:7][N:6]=1.Cl[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:12][C:11]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[Se:1][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 4

HCID 7751Ethyl chloroacetateHCID 73973Sodium selenideHCID 810792-ChloronicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 59547216HCID 59547216, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium selenide (0.9 g, 7.2 mmol, prepared from 0.75 g of selenium as described above) in DMF (7 mL) was added a solution of 2-chloropyridine-3-carbonitrile (1 g, 7.2 mmol) in DMF (3 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then ethyl chloroacetate (0.78 mL, 7.22 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (0.39 g, 7.2 mmol) in methanol (7 mL) was added dropwise and stirring was continued for 1 h at the same temperature. The mixture was allowed to room temperature (rt) and poured into cold water and stirred for 15 min. The precipitated solid was filtered, washed with water and dried to give the product as a yellow color solid (1.5 g, 77%), mp 194-196° C. 1H NMR (400 MHz, CDCl3): δ 8.65 (1H, dd, J=4.6, 1.4 Hz, H-6), 7.86 (1H, dd, J=8.2, 1.4 Hz, H-4), 7.33 (1H, dd, J=8.2, 4.6 Hz, H-5), 6.04 (2H, br s, —NH2), 4.34 (2H, q, J=7.1 Hz, —COOCH2CH3), 1.38 (3H, t, J=7.1 Hz, —COOCH2CH3); LC-MS (positive ion mode): m/z 269, 271 (M+H)+.

Workup

  1. stirringagain stirred at 60-70° C. for 2 h
  2. stirringstirring
  3. waitwas continued for 1 h at the same temperature
  4. customwas allowed to room temperature
  5. custom(rt)
  6. stirringstirred for 15 min
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-fa60355edf2645deb10a71f8da756b7e
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

Loading…