2-AMino-4-[(4-fluorobenzyl)aMino]-1-nitrobenzene

2-AMino-4-[(4-fluorobenzyl)aMino]-1-nitrobenzene - Names and Identifiers

Name	2-Amino-4-[(4-fluorobenzyl)amino]-1-nitrobenzene
Synonyms	Retigabine Impurity 5 2-Amino-4-[(4-fluorobenzyl)amino]-1-nitrobenzene 2-AMino-4-[(4-fluorobenzyl)aMino]-1-nitrobenzene N1-[(4-Fluorophenyl)methyl]-4-nitro-1,3-benzenediamine 1,3-Benzenediamine, N1-[(4-fluorophenyl)methyl]-4-nitro- 2-AMino-4-[(4-fluorobenzyl)aMino]-1-nitrobenzene(RETIGABINE inteMediate)
CAS	1263404-74-5
EINECS	2017-001-1

2-AMino-4-[(4-fluorobenzyl)aMino]-1-nitrobenzene - Physico-chemical Properties

Molecular Formula	C13H12FN3O2
Molar Mass	261.25
Density	1.390±0.06 g/cm3(Predicted)
Melting Point	175-177°C
Boling Point	464.9±45.0 °C(Predicted)
Solubility	DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
Appearance	Solid
Color	Yellow to Dark Yellow
pKa	0.22±0.35(Predicted)
Storage Condition	Refrigerator

2-AMino-4-[(4-fluorobenzyl)aMino]-1-nitrobenzene - References

Application

2-amino -4-[(4-fluorobenzyl) amino]-1-nitrobenzene is useful as an intermediate in the synthesis of pharmaceuticals. For example, the preparation of retegabine, an antiepileptic drug with multiple mechanisms such as neuronal potassium channel openers and GABA enhancers.

preparation

compound (VI)(60.6g,0.1mol) was dissolved in ethanol (400mL), water (120mL). Concentrated hydrochloric acid (160mL) was added into 1L reaction bottle, stirred at 70~80 ℃ for 1 hour, and the reaction solution was red and clarified, then cooled to 10 ℃, the pH was adjusted to Neutral with 4molL-1 sodium hydroxide solution, and the filter cake was washed with water and dried by Suction filtration to obtain 2-amino -4-[(4-fluorobenzyl)] as a yellow solid. Amino]-1-nitrobenzene 51.2g, yield 98%,mp112~113 °c.

Last Update：2024-04-09 02:00:15