Trifluoroacetic acid → 5-(2-Chloroethyl)Oxindole

HRID 1066737Notes

Reaction equation

HRID 1066737 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[Cl:1][CH2:2][CH2:3][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 145813925-(2-Chloroethyl)Oxindole

Procedure

To a 100 ml round-bottomed flask equipped with condenser and nitrogen inlet were added 5.0 grams (23.9 mmol) of 5-chloroacetyl oxindole and 18.5 ml triflouroacetic acid. To the stirring solution was added 8.77 ml (54.9 mmol) of triethylsilane while cooling to prevent exotherm, and the reaction stirred 16 hours at room temperature. The reaction was then poured into ice water, stirred and the beige solid filtered, washed with water and hexane, and dried to give 5-(2-chloroethyl)oxindole, m.p. 168°-170° C., 3.0 grams (64%).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperaturewhile cooling
  3. stirringstirred
  4. filtrationthe beige solid filtered
  5. washwashed with water and hexane
  6. customdried

Sources & evidence

ORD record
ord-c80bcac74a494c1c9ad7a014959f069d
Source dataset
uspto-grants-2001_06
Patent number
US06245766B1

Reaction notes

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