Trifluoroacetic acid → 2-(2-Pyrazinyl)aniline

HRID 1816279Notes

Reaction equation

HRID 1816279 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13]C(=O)OC(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 22493234Tert-butyl 2-(2-pyrazinyl)phenylcarbamate

Product 1

HCID 224932822-(2-Pyrazinyl)anilineYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-(2-pyrazinyl)phenylcarbamate (0.62 g, 2.29 mmol), dichloromethane (10 mL), and anisole (1 mL) was added trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 4 h and allowed to stand at room temperature overnight. The reaction mixture was concentrated in vacuo to give 0.41 g of 2-(2-pyrazinyl)aniline, which was coupled with CMI (0.20 g, 1.3 mmol), under conditions described in the general procedure for CMI couplings, to give 0.022 g of N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-(2-pyrazinyl)aniline.

Workup

  1. waitto stand at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e7ee31c679e040fda62ca9f4dc84f780
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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