Iodoethane → HCID 22124667, compound

HRID 1857958Notes

Reaction equation

HRID 1857958 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](I)[CH3:20]>CN(C=O)C>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[N:9]2[CH2:19][CH3:20])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 22124593HCID 22124593, compound

Product 1

HCID 22124667HCID 22124667, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (XII) (2.1 g, 13 mmol) in dry DMF (65 mL) was added cesium carbonate (6.4 g, 19.6 mmol), followed by ethyl iodine (1.71 mL, 21.4 mmol), and the mixture was stirred at 60° C. for 4.5 hours. The cooled mixture was filtered, and the filtrate was diluted with ethyl acetate. The solution was washed with brine, dried, and concentrated to give an orange residue that was purified by silica gel chromatography, eluting with 1:1 ethyl acetate: hexanes and then ethyl acetate. Concentration of product fractions gave 7-amino-1-ethyl-1H-[1,6]naphthyridin-2-one (XIII) (1.3 g, 53%).

Workup

  1. filtrationThe cooled mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washThe solution was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an orange residue that
  7. customwas purified by silica gel chromatography
  8. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-09ff5f61814d4345b967d9e290e6db22
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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