ChemicalBook CAS DataBase List 4-NITROANILINE HYDROCHLORIDE

4-NITROANILINE HYDROCHLORIDE synthesis

8synthesis methods

Product Name:4-NITROANILINE HYDROCHLORIDE
CAS Number:15873-51-5
Molecular formula:C6H7ClN2O2
Molecular Weight:174.58

100-25-4

15873-51-5

GENERAL METHOD: To a 0.6 mL THF solution of the nitro compound (2 mmol) was added Fe(acac)3 (10 mol%, 70 mg) and TMDS (1.5 eq., equivalent to tris-Si-H, 0.53 mL). The reaction mixture was heated under constant stirring for 24 hours (unless otherwise stated). Upon completion of the reaction, the reaction mixture was diluted with a minimal amount of Et2O. Subsequently, a solution of Et2O with HCl (2 equivalents) was added dropwise. After precipitate generation was observed, stirring was continued for 5 minutes and then filtered. The precipitate was washed several times with Et2O and dried to give 4-nitroaniline hydrochloride.

100-25-4 Synthesis

100-25-4
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15873-51-5
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Yield: 95%

Reaction Conditions:

Stage #1:para-dinitrobenzene with iron(III) acetylacetonate;1,1,3,3-Tetramethyldisiloxane in tetrahydrofuran at 60; for 48 h;Inert atmosphere;Sealed tube;
Stage #2: with hydrogenchloride in tetrahydrofuran;diethyl ether for 0.0833333 h;

Steps:

4.1. General
General procedure: In a solution of nitro compound (2 mmol) in 0.6 mL of THF were added Fe(acac)₃ (10 mmol %, 70 mg) and TMDS (1.5 equiv or three Si-H, 0.53 mL). After 24 h (unless otherwise indicated) under heating the reaction mixture was diluted in a minimum of Et₂O with a constant stirring. HCl (2 equiv) in Et₂O was then added dropwise. A precipitate appears; the mixture was stirred for 5 min and filtered. It was washed several times with Et₂O and dried to afford the desired product as a hydrochloride salt.

References:

Pehlivan, Leyla;Métay, Estelle;Laval, Stéphane;Dayoub, Wissam;Demonchaux, Patrice;Mignani, Gérard;Lemaire, Marc [Tetrahedron,2011,vol. 67,# 10,p. 1971 - 1976] Location in patent:experimental part