Trifluoroacetic acid → 2-(1H-indol-3-yl)propanenitrile

HRID 736074Notes

Reaction equation

HRID 736074 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]([CH3:20])[C:18]#[N:19])=[CH:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]([CH3:20])[C:18]#[N:19])=[CH:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 252230692-(1-Tert-butoxycarbonylindol-3-yl)propionitrile

Product 1

HCID 122007942-(1H-indol-3-yl)propanenitrileYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-(1-tert-butoxycarbonylindol-3-yl)propionitrile (4.00 g, 14.8 mmol) in DCM (10 mL) was added TFA (10 mL) with caution. After 1 hour, the reaction was diluted with DCM (40 mL), washed with water (2×40 mL) and brine, then dried (Na2SO4), and concentrated under reduced pressure to give 2-(1H-indol-3-yl)propionitrile (2.5 g, 99%) as a pale brown solid; 1H-NMR (CDCl3): δ 8.25 (1H, d), 7.69 (1H, s), 7.65 (1H, d), 7.45 (1H, app t), 7.37 (1H, app t), 4.12 (1H, q), 1.79 (3H, d).

Workup

  1. washwashed with water (2×40 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4662412833904abd87ca8b2a374b9b8e
Source dataset
uspto-grants-2009_09
Patent number
US07595311B2

Reaction notes

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