3-(Trifluoromethyl)aniline → HCID 17992837, compound

HRID 1803771Notes

Reaction equation

HRID 1803771 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:12]([C:18]([O:20][CH3:21])=[O:19])#[C:13][C:14]([O:16][CH3:17])=[O:15]>CO>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([NH:6]/[C:13](=[CH:12]/[C:18]([O:20][CH3:21])=[O:19])/[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 17992837HCID 17992837, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Trifluoromethyl)aniline (10.0 g, 62.0 mmol) and dimethyl acetylenedicarboxylate (8.4 mL, 68.4 mmol) were dissolved in methanol (100 mL) and the mixture was refluxed for 2 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel eluting with 0-30% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 3.71 (s, 3H), 3.73 (s, 3H), 5.49 (s, 1H), 7.16 (m, 2H), 7.36 (d, J=7.80 Hz, 1H), 7.48 (t, J=7.80 Hz, 1H). MS (ESI) m/z 303.97 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue was chromatographed on silica gel eluting with 0-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7a1821d3584f46ba8b03148493c7d8f1
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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