Propargyl bromide → Aniline

HRID 40734Notes

Reaction equation

HRID 40734 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:13]([Br:16])[C:14]#[CH:15]>C1(C)C=CC=CC=1>[Br:16][CH2:13][C:14]1[N:3]=[N:2][N:1]([C:4]2[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=2)[CH:15]=1.[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 7842Propargyl bromideHCID 1370491-Azido-4-nitrobenzene

Product 2

HCID 6115AnilineHCID 68775883HCID 68775883, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-azido-4-nitrobenzene (0.5 g, 3.0 mmol), propargyl bromide (80% in toluene) (0.7 mL, 0.6 mmol) and toluene (3 mL) in a sealed tube was heated to 60° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated to give two inseparable isomers 4-(4-(bromomethyl)-1H-1,2,3-triazol-1-yl)aniline and 445-(bromomethyl)-1H-1,2,3-triazol-1-yl)aniline in a 2/1 ratio (as judged by analytical HPLC analysis) which were hydrogenated to afford a mixture of 4-(4-methyl-1H-1,2,3-triazol-1-yl)aniline and 4-(5-methyl-1H-1,2,3-triazol-1-yl)aniline.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d0dbf283b57547a5a5301f7c7fff1203
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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