Trifluoroacetic acid → 5-(2-Chloroethyl)Oxindole

HRID 1639271Notes

Reaction equation

HRID 1639271 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 N2 inlet were added 5.0 g (23.9 mmol) of 5-chloroacetyl oxindole and 18.5 ml trifluoroacetic 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 g (64%).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturewhile cooling
  3. stirringstirred
  4. filtrationthe beige solid filtered
  5. washwashed with water and hexane
  6. customdried

Sources & evidence

ORD record
ord-ba7ab63fdc354dc3ac3bcd3562d7657a
Source dataset
uspto-grants-1989_11
Patent number
US04883795

Reaction notes

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