ChemicalBook CAS DataBase List 4-(4-Fluorobenzylamino)-1,2-phenylenediamine

4-(4-Fluorobenzylamino)-1,2-phenylenediamine synthesis

6synthesis methods

Product Name:4-(4-Fluorobenzylamino)-1,2-phenylenediamine
CAS Number:491871-67-1
Molecular formula:C13H14FN3
Molecular Weight:231.27

2-Amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene

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4-(4-Fluorobenzylamino)-1,2-phenylenediamine

491871-67-1
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Yield:491871-67-1 99.6%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in tetrahydrofuran

Steps:

4.1 4.1. Synthesis of tert-butyl 2-(tert-butoxycarbonyl imino)-4-(N-parafluorobenzyl-imino)-aniline formate
Preparation example4: synthesis of ethyl 2-amino-4-(N-parafluorobenzyl-N-allyl-imino) -aniline formate (K20) _{RRN 54,59}4.1. Synthesis of tert-butyl 2-(tert-butoxycarbonyl imino)-4-(N-parafluorobenzyl-imino)-aniline formate
According to a procudure similar to that of Preparation example 1, intermediate 2-nitro -4-(N-parafluorobenzyl-imino)-aniline was obtained by using o-nitro paraphenylene diamine and parafluorobenzaldehyde as starting materials. 2-nitro-4-(N-parafluorobenzyl-imino)-aniline (2.61g, 0.01mol) was dissolved in THF (30mL) and air therein was replace with N₂.
Then Pd-C (10%, 261mg) was rapidly added and N₂ therein was replaced with H₂.
The hydrogenation reaction was conducted overnight, and the resulting resction solution was filtered and concentrated to produce a product of 2-amino-4-(N-parafluorobenzyl-imino)-aniline (2.3g, 99.6%, colorless oil, instable, prone to be oxidized and deteriorated), which was rapidly used in nest step. ¹H NMR(300 MHz, CDCl₃): δ 7.32(t, J=8.7Hz, 2H), 7.02(t, J=8.7Hz, 2H), 6.58(d, J=8.7Hz, 1H), 6.01-6.08(m, 2H), 4.22(s, 2H).

References:

Shanghai Institute Materia Medica, Chinese Academy Of Sciences;NAN, Fajun;LI, Min;GAO, Zhaobing;CHEN, Fei;ZHANG, Yangming;ZHOU, Pingzheng;HU, Haining;XU, Haiyan;LIU, Sheng EP2772481, 2014, A1 Location in patent:Paragraph 0051-0052

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