Ethyl chloroacetate → HCID 53739137, compound

HRID 1164531Notes

Reaction equation

HRID 1164531 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([Cl:12])=[C:7]([NH2:11])[CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([Cl:12])=[C:7]([NH2:11])[CH:8]=2)[N:3]1[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 2046666477859-59-7

Product 1

HCID 53739137HCID 53739137, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-oxo-5-amino-6-chloroindoline (3.2 g), potassium carbonate (4.8 g) and acetone (60 ml) was added dropwise ethyl chloroacetate (3.2 g) at ambient temperature. The reaction mixture was refluxed with stirring for 4 hours and then filtered under warm condition. The filter cake was washed with acetone. The combined filtrate and washings were concentrated under reduced pressure to give a residue, which was purified by a column chromatography on silica gel to give crystalline ethyl 2-oxo-5-amino-6-chloro-1-indolineacetate (0.9 g).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. filtrationfiltered
  3. temperatureunder warm condition
  4. washThe filter cake was washed with acetone
  5. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  6. customto give a residue, which
  7. customwas purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-e2fa5a2c04444ddf9ab904d5f9e53a1d
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

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