Trifluoroacetic acid → 1-(Cyanomethyl)indoline

HRID 2057359Notes

Reaction equation

HRID 2057359 reaction equation
[C:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)#[N:2].FC(F)(F)C(O)=O.N1C2C(=CC=CC=2)C=C1.B>B.C1COCC1>[C:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 122309041H-Indole-1-acetonitrileHCID 178419140HCID 178419140, compound

Product 1

HCID 124246651-(Cyanomethyl)indoline

Reagents, catalysts & solvents 1

HCID 2723981Borane;tetrahydrofuranSolvent

Procedure

In an operation carried out in a manner similar to that described in Example XIV, 105 milligrams of 1-cyanomethyl indole was dissolved in 1.5 milliliters of 1 M BH3.THF under nitrogen. Then, while cooling and stirring in an ice bath, 1.0 milliliter of trifluoroacetic acid was added dropwise to the indole-borane reagent mixture and after completion of the addition, stirring was continued for 1.5 hours while maintaining nitrogen atmosphere to obtain a 1-cyanomethyl-2,3-dihydroindole product in the reaction mixture. The product was recovered by adding first water, then methylene chloride, stirring the mixture (about 15 minutes), making alkaline (pH>9), separating the methylene chloride solution, drying the latter and evaporating the solvent from the dried solution in vacuo.

Workup

  1. temperatureThen, while cooling
  2. additionafter completion of the addition
  3. stirringstirring
  4. temperaturewhile maintaining nitrogen atmosphere

Sources & evidence

ORD record
ord-855f82f2e688447391a16ae73904aff6
Source dataset
uspto-grants-1980_07
Patent number
US04210590

Reaction notes

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