Synthesis of 3-nitroaniline (m-nitroaniline, meta-nitroaniline)

Preparation of 3-nitroaniline

Preparation of m-nitroaniline

Preparation of m-nitroaniline

500 ml of water are heated to 85° C in a glass beaker of 2-l capacity, 100 g dinitrobenzene are then added with very efficient stirring. 245 g of crystallized sodium sulfide (Na2S · 9H2O) dissolved in 200 ml of water are then allowed to run into this emulsion of dinitrobenzene from a dropping funnel during 10 minutes. The dinitrobenzene is partially reduced by sodium sulfide, m-nitraniline being formed. The end-point of the reaction may be recognized by the fact that a drop of the solution on a filter paper gives a black streak of metallic sulfide with an iron or copper sulfate solution. As soon as the reduction reaction is complete, the mixture is cooled at once to 20° C by throwing in 500 g of ice, and, after standing for several hours the m-nitroaniline is filtered off; it may be recrystallized from boiling water, but for most purposes this is unnecessary. The yield is about 55 g pure recrystallized m-nitraniline, mp.p. 114° C.

The fundamental processes of dye chemistry, by F. David, 66, 1921

Preparation of 3-nitroaniline (m-nitroaniline, meta-nitroaniline)

Preparation of 3-nitroaniline (m-nitroaniline, meta-nitroaniline)

10 g of m-dinitrobenzene is dissolved in 40 g of ethanol and the solution is cooled down, upon which a portion of the m-dinitrobenzene separates out. This solution is further treated with 8 g of concentrated ammonium hydroxide solution (each 1 g of m-dinitrobenzene requires 0.8 g of concentrated ammonium hydroxide solution). The reaction flask with its content is tared, the mixture is saturated with hydrogen sulfide at room temperature and after saturation is complete the flask is heated under reflux for 30 minutes. Then the reaction flask content is cooled to room temperature and hydrogen sulfide again passed into it to solution until there is an increase of 6 g in weight (or 0.6 g for every gram of m-dinitrobenzene used). If correct weight is not reached hydrogen sulfide is again passed into the mixture. The solution is diluted with water, the precipitated crude 3-nitroaniline is filtered, washed with water, and extracted by warming with dilute hydrochloric acid. 3-Nitroaniline hydrochloride is converted to 3-nitroaniline base by neutralizing with ammonium hydroxide. Finally 3-nitroaniline is recrystallized from water yielding 70-80% of product which melts at 114° C.

The practical methods of organic chemistry, by L. Gattermann, 192-193, 1909

IUPAC Name

3-nitroaniline

InChI

InChI=1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2

InChI Key

XJCVRTZCHMZPBD-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC(=C1)[N+](=O)[O-])N

MeSH Synonyms

3-NA, aniline, 3-nitroaniline

Depositor-Supplied Synonyms

3-Nitroaniline, M-NITROANILINE, 99-09-2, Benzenamine, 3-nitro-, 3-Nitrophenylamine, 3-Aminonitrobenzene, Nitranilin, Fast Orange Base R, Devol Orange R, Azobase MNA, m-Nitrophenylamine, 3-Nitrobenzenamine, m-Aminonitrobenzene, m-Nitroaminobenzene, 1-Amino-3-nitrobenzene, Aniline, m-nitro-, Fast Orange M Base, Fast Orange R Base, Fast Orange R Salt, Orange Base Irga I, Daito Orange Base R, Diazo Fast Orange R, Fast Orange MM Base, m-Nitraniline, Naphtoelan Orange R Base, Amarthol Fast Orange R Base, Hiltonil Fast Orange R Base, C.I. Azoic Diazo Component 7, Nitroaniline, 3-, 3-Nitro-phenylamine, 3-NITRO-ANILINE, C.I. 37030, NSC 9574, CI Azoic Diazo Component 7, CCRIS 2318, HSDB 2570, XJCVRTZCHMZPBD-UHFFFAOYSA-N, EINECS 202-729-1, CI 37030, AI3-52474, AC-907/25014117, SMR000343223, m-nitro aniline, m-nitro-aniline, meta-Nitroaniline, 3-nitro aniline, 3-Nitrobenzeneamine, (3-nitrophenyl)-amine, AC1L1OQA, AC1Q5AUF, WLN: ZR CNW, DSSTox_CID_5725, AC1Q51DY, SCHEMBL1487, N9829_ALDRICH, DSSTox_RID_77894, UNII-CM50SM561T, DSSTox_GSID_25725, ghl.PD_Mitscher_leg0.915, KSC486M5J, MLS000517063, MLS002415745, UN 1661 (Salt/Mix), CHEMBL14068, 442392_SUPELCO, 45989_RIEDEL, CM50SM561T, SCHEMBL12707526, 45989_FLUKA, 72670_FLUKA, CTK3I6654, NSC9574, MolPort-000-645-308, HMS2666G03, NSC-9574, STR01954, Tox21_200386, ANW-13673, AR-1F4639, BBL009055, SBB058851, STL137655, ZINC00047987, m-Nitroaniline [UN1661] [Poison], AKOS000119115, AS01505, LS-2057, m-Nitroaniline [UN1661] [Poison], MCULE-8885530793, MP-2175, RP20414, RTC-050904, CAS-99-09-2, NCGC00091126-01, NCGC00091126-02, NCGC00257940-01, AJ-09065, AK-96015, CJ-00289, KB-32962, SC-22889, ZB001426, AB1002013, DB-057758, ST2410819, TC-050904, FT-0616230, N0117, ST45255276, AZ0001-0094, 43337-EP2281563A1, 43337-EP2281815A1, 43337-EP2308833A2, 43337-EP2311829A1, I01-1869, 3B3-020153, T0517-8618, InChI=1/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H, 12262-63-4

Removed Synonyms

null, CID7423, UN1661, T275, MNA, 2096-10-8

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