Synthesis of m-anisidine

Preparation of m-anisidine

A mixture of 35 g. (0.23 mole) of m-nitroanisole (p. 213), 110 ml. of methanol, and 7.5 ml. of concentrated hydrochloric acid is stirred and heated to boiling. Forty-two grams (0.75 gram atom) of iron filings is added in small portions over a 1-hour period, and refluxing and stirring are continued for 5 additional hours. The mixture is made strongly alkaline with sodium hydroxide and steam-distilled, the methanol which first distils over being collected separately. The remainder of the distillate is extracted with ether; the ethereal solu­tion is dried over anhydrous sodium sulfate and distilled. m-Anisidine (23.2 g. or 80%) is collected at 125°/13 mm.

Reference: J. Chem. Soc, 1934, 1420; J. Chem. Soc, 127, 494 (1925).

IUPAC Name

3-methoxyaniline

InChI

InChI=1S/C7H9NO/c1-9-7-4-2-3-6(8)5-7/h2-5H,8H2,1H3

InChI Key

NCBZRJODKRCREW-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=CC(=C1)N

MeSH Synonyms

3-methoxyaniline

Depositor-Supplied Synonyms

m-Anisidine, 3-METHOXYANILINE, 536-90-3, 3-Aminoanisole, m-Methoxyaniline, 3-Methoxybenzenamine, 3-Anisidine, m-Aminoanisole, Benzenamine, 3-methoxy-, m-Anisylamine, 1-Amino-3-methoxybenzene, UNII-JXA144KX2I, NSC 7631, 3-Methoxy aniline, 3-methoxyphenylamine, CCRIS 5886, 3-Methoxy-phenylamine, EINECS 208-651-4, BRN 0386119, JXA144KX2I, AI3-52519, NCBZRJODKRCREW-UHFFFAOYSA-N, Q-200384, meta-anisidine, HSDB 7816, 3-methoxylaniline, m-methoxy aniline, 3-methoxy-aniline, m-Aminomethoxybenzene, 3-(methyloxy)aniline, 3-methoxy-benzenamine, (3-methoxyphenyl)amine, PubChem12919, ACMC-1ANQF, (3-methoxyphenyl)-amine, 3′-AMINOPHENETOL, 3-Methoxy-1-aminobenzene, DSSTox_CID_4529, 3-Aminophenol methyl ether, AC1L1W0Z, DSSTox_RID_77445, AKOS BBB/405, DSSTox_GSID_24529, SCHEMBL66692, 5-METHOXYPHENYL AMINE, A88204_ALDRICH, 4-13-00-00953 (Beilstein Handbook Reference), KSC271M2H, MLS001050108, CHEMBL1500995, DTXSID8024529, 10480_FLUKA, CTK1H1623, TIMTEC-BB SBB040499, NSC7631, MOLARCH MA_0100121, MolPort-000-146-017, OTAVA-BB 1314576, OTAVA-BB 1314579, 3-AMINOPHENYL METHYL ETHER, BB_SC-7166, LABOTEST-BB LTBB000511, LABOTEST-BB LTBB000784, ZINC157531, BB_SC-07166, NSC-7631, ZX-AT007002, AKOS BBS-00003677, Tox21_200820, ANW-31833, BBL011599, DT1781, LABOTEST-BB LT03333242, MFCD00007783, SBB040499, STL163332, ZINC00157531, AKOS000119110, AM87044, AS01512, CS19943, FCH2250714, LS-1331, MCULE-1820278837, OR28775, PS-4590, RP19519, RTC-050915, TRA0026624, ACM17920353, NCGC00091221-01, NCGC00091221-02, NCGC00258374-01, AC-10034, AJ-15050, AK-48321, AN-45695, BBV-38790051, CAS-536-90-3, CJ-01680, KB-32514, OR034073, OR163436, SC-05155, SMR000112350, ZB006714, BB0295696, DB-050406, ST2410760, TC-050915, A0485, FT-0628164, ST45255318, A15634, M-5969, 79526-EP2305695A2, 79526-EP2305696A2, 79526-EP2305697A2, 79526-EP2305698A2, I01-0551, T7100133, F2190-0440, UNII-6DE9L863GO component NCBZRJODKRCREW-UHFFFAOYSA-N, InChI=1/C7H9NO/c1-9-7-4-2-3-6(8)5-7/h2-5H,8H2,1H, 918666-97-4

Removed Synonyms

m-Phenetidine, Cerous carbonate, 3-Ethoxybenzenamine, (3-ethoxyphenyl)amine, Aniline, 3-methoxy-, 3-ETHOXYANILINE, C7H9NO, Benzenamine, 3-ethoxy-, 2-Amino-6-methoxypyridine, 2-Amino-6-methoxy pyridine, 3-Methoxy-3-methyl-1-butanol, C7-H9-N-O, CID10824, NA2431, UN2431, C004521, 17920-35-3

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