2,2-Dimethylsuccinic anhydride → HCID 57516716, compound

HRID 1917533Notes

Reaction equation

HRID 1917533 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1([CH3:17])[CH2:14][C:13](=O)[O:12][C:11]1=[O:16]>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:12])[CH2:14][C:10]([CH3:17])([CH3:9])[C:11]2=[O:16])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 870672,2-Dimethylsuccinic anhydrideHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 57516716HCID 57516716, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

5-iodopyridin-2-amine (1 g, 4.55 mmol) was dissolved in DMF (5 ml) and 3,3-dimethyldihydrofuran-2,5-dione (1.28 g, 10.0 mmol, 2.2 equiv.) was added at room temperature. The mixture was stirred for 3 hr at 150° C. The reaction mixture was evaporated to dryness and loaded directly to a silica gel column. The crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 1-(5-iodopyridin-2-yl)-3,3-dimethylpyrrolidine-2,5-dione (1.3 g, 3.94 mmol, 86.6% yield) was obtained as a yellow solid, MS: m/e=331.0 (M+H+).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customThe crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0)

Sources & evidence

ORD record
ord-bceb57af3c8c474d95278d18060478ed
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

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