2-(4-nitrobenzyl)-2H-1,2,3-benzotriazole → 4-(2H-1,2,3-benzotriazol-2-ylmethyl)aniline

HRID 30700Notes

Reaction equation

HRID 30700 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]2[N:13]=[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]3=[N:10]2)=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C(O)C>[N:10]1[N:9]([CH2:8][C:7]2[CH:18]=[CH:19][C:4]([NH2:1])=[CH:5][CH:6]=2)[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=12

Participants

4

Reactant 1

HCID 37040502-(4-nitrobenzyl)-2H-1,2,3-benzotriazole

Product 1

HCID 692091984-(2H-1,2,3-benzotriazol-2-ylmethyl)anilineYield 35.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(4-nitrobenzyl)-2H-1,2,3-benzotriazole (1.0 g), 10% palladium carbon (100 mg) and ethanol (20 ml) was stirred under a hydrogen atmosphere at room temperature for 4 hrs. Palladium carbon was removed from the reaction mixture by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 4-(2H-1,2,3-benzotriazol-2-ylmethyl)aniline (313 mg, 35%) as crystals from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 229-230° C.

Workup

  1. customPalladium carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-be6ec87a9614492e99082f1aa99e7a4b
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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