Aniline → N-prop-2-ynylaniline

HRID 2377277Notes

Reaction equation

HRID 2377277 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C>[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 6115AnilineHCID 7842Propargyl bromide

Product 1

HCID 305815N-prop-2-ynylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of propargyl bromide (0.11 mL, 1 mmol) and aniline (0.46 mL, 5 mmol) in ethanol (2 mL) was stirred at room temperature for about 5 days. The solvent was concentrated under vacuum and the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent to provide Example 640. MS (ESI): m/z 132 (M+H)+.

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. customthe residue was purified by flash chromatography on silica gel
  3. customto provide Example 640

Sources & evidence

ORD record
ord-fd28749316c04ae199601df768abe60e
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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