Chloroacetamide → 2-(2,3-Dioxo-2,3-dihydro-1H-indol-1-yl)acetamide

HRID 2383616Notes

Reaction equation

HRID 2383616 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].C([O-])([O-])=O.[K+].[K+].Cl[CH2:19][C:20]([NH2:22])=[O:21]>CN(C=O)C>[O:3]=[C:2]1[C:4](=[O:5])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]1[CH2:19][C:20]([NH2:22])=[O:21]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 7054IsatinHCID 11430Potassium Carbonate

Product 1

HCID 19061622-(2,3-Dioxo-2,3-dihydro-1H-indol-1-yl)acetamideYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of isatin (5.0 g, 35 mmol), K2CO3 (5.5 g, 40 mmol) and chloroacetamide (3.74 g, 40 mmol) in a 100 mL of flask was added DMF (25 mL). The resulting mixture was heated at 90° C. (oil temp.) for 2 h. After cooling to rt, it was poured onto ice/H2O (200 mL) and the resulting precipitate was collected by suction filtration to give 2-(2,3-dioxoindolin-1-yl)acetamide (4.32 g) after drying. 1H NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.65 (t, J=7.6 Hz, 1H), 7.58 (d, J=7.2 Hz, 1H), 7.30 (s, 1H), 7.14 (t, J=7.4 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 4.25 (s, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. additionit was poured onto ice/H2O (200 mL)
  3. filtrationthe resulting precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-3a60803dba754338b0d272b71d5a7ea2
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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