Ethyl Acetate → 1-Acetyl-3-(1-ethoxy-1-phenylmethylidene}-2-indolinone

HRID 1637918Notes

Reaction equation

HRID 1637918 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13])(=[O:3])[CH3:2].[CH2:14]([O:16][C:17](=O)[CH3:18])[CH3:15]>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[C:14]([O:16][CH2:17][CH3:18])[C:15]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:5]1=[O:13])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 3237191-Acetylindolin-2-one2×

Product 1

HCID 542378881-Acetyl-3-(1-ethoxy-1-phenylmethylidene}-2-indolinone

Procedure

Yield: about 67% of theory, the product contains about 25 to 34% of 1-acetyl-2-indolinone. Melting point: 123-129° C. (with an amount of 34% of 1-acetyl-2-indolinone). An insoluble fraction is isolated from the above mixture by combining with ethylacetate, extracting with dilute aqueous sodium carbonate solution and with water and by filtering, this fraction being the pure product. Melting point: 187-189° C.; C19H17NO3 ; Calc.: C, 74.25; H, 5.57; N, 4.56; Found: 73.95; 5.57; 4.53.

Workup

  1. customAn insoluble fraction is isolated from the above mixture
  2. extractionextracting with dilute aqueous sodium carbonate solution and with water
  3. filtrationby filtering

Sources & evidence

ORD record
ord-b8a20e71ae414949967c2d968d2c2f0a
Source dataset
uspto-grants-2000_03
Patent number
US06043254

Reaction notes

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