Synthesis of methyl anthranilate

Preparation of methyl anthranilate

Methyl anthranilate is prepared by esterification of anthranilic acid or N-acetylanthranilic acid.

Preparation of methyl anthranilate

Preparation of methyl anthranilate

To the round bottom flask fitted with reflux condenser, which is protected from moisture with a calcium chloride tube, 7 g of anthranilic acid are suspended in 50 ml of dry methyl alcohol. Dry hydrogen chloride is passed until the solution is saturated and becomes hot, then the reaction mixture is refluxed for one hour. When the reaction is complete the solution is cooled and methyl anthranilate hydrochloride crystallizes. The mixture is diluted with 200 ml of water and made alkaline by the solution of sodium carbonate. The oily methyl anthranilate is extracted with ether and the extract washed with 5 % sodium carbonate solution, and then with water. The extract is dried over sodium sulfate and evaporated to small bulk. The distillation in vacuum and collecting fraction boiling at 135° C (15 mm of Hg), yields a crystalline mass melting at 24.5° C.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 32-33, 1923

IUPAC Name

methyl 2-aminobenzoate

InChI

InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3

InChI Key

VAMXMNNIEUEQDV-UHFFFAOYSA-N

Canonical SMILES

COC(=O)C1=CC=CC=C1N

MeSH Synonyms

methyl anthranilate

Depositor-Supplied Synonyms

Methyl 2-aminobenzoate, METHYL ANTHRANILATE, 134-20-3, 2-Aminobenzoic acid methyl ester, Methyl o-aminobenzoate, Nevoli oil, Anthranilic acid methyl ester, o-Carbomethoxyaniline, 2-Carbomethoxyaniline, Methylanthranilate, 2-(Methoxycarbonyl)aniline, Benzoic acid, 2-amino-, methyl ester, Anthranilic acid, methyl ester, O-methyl anthranilate, Neroli oil, artifical, Neroli oil, artificial, o-Aminobenzoic acid methyl ester, NSC 3109, Amino methyl benzoate, o-, Methyl anthranilate (natural), METHYL-2-AMINOBENZOATE, UNII-981I0C1E5W, FEMA No. 2682, CCRIS 1349, Methylester kyseliny anthranilove, CHEBI:73244, HSDB 1008, o-Aminobenzoic acid, methyl ester, 2-amino-benzoic acid methyl ester, 2-Aminobenzoic acid, methyl ester, VAMXMNNIEUEQDV-UHFFFAOYSA-N, EINECS 205-132-4, Epa Pesticide Chemical Code 128725, BRN 0606965, Methylester kyseliny anthranilove [Czech], AI3-01022, DSSTox_CID_5567, DSSTox_RID_77832, DSSTox_GSID_25567, CAS-134-20-3, methyl aminobenzoate, NEROLI, o-methoxycarbonylaniline, PubChem13629, o-Amino methyl benzoate, methyl 2-amino-benzoate, AC1L1REA, AC1Q5ZBB, ACMC-209bu5, WLN: ZR BVO1, Anthranilic acid methylester, PS2055_SUPELCO, AC1Q42HZ, SCHEMBL57713, METHYL 2-ANTHRANILATE, KSC115A6D, W268208_ALDRICH, W268216_ALDRICH, 236454_ALDRICH, Jsp002075, CHEMBL1493986, 10730_FLUKA, CTK0B5061, FEMA 2682, NSC3109, 2-amino benzoic acid methyl ester, MolPort-000-004-891, OTAVA-BB 1867348, 981I0C1E5W, BB_SC-2799, LABOTEST-BB LTBB000479, Benzoic acid, amino-, methyl ester, Methyl ester of o-Aminobenzoic acid, NSC-3109, ANTHRANILIC ACID:METHYL ESTER, Tox21_201657, Tox21_300347, ANW-19611, AR-1J5742, BBL027653, LS-775, SBB059788, STK045541, ZINC00157525, AKOS000119222, AS01236, MCULE-3500477192, RP21463, RTR-033354, NCGC00091409-01, NCGC00091409-02, NCGC00091409-03, NCGC00254347-01, NCGC00259206-01, AC-11600, AJ-15047, AK-41339, AN-23083, BENZOIC ACID METHYL ESTER,2-AMINO, CJ-01677, KB-54722, SC-11429, ZB006711, DB-042220, KB-228184, ST2413278, TL8006109, TR-033354, A0500, FT-0622414, ST45255311, C20634, M-5862, I01-6584, 3B3-030299, InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H, 143202-08-8

Removed Synonyms

Benzoic acid, methyl ester, CID8635, Aminoterephthalic acid dimethyl ester, 4-14-00-01008 (Beilstein Handbook Reference), 135-01-3, 13511-38-1

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1 comment

  1. Adolf Todros.

    Dear Sirs,

    WE need:
    1) To know the method of transforming natural Dimethyl Anthranelate to Methyl Anthranelate, chemically or by Enzymes.

    2) If there are chemical companies can do this transformation for us on toll basis.

    Thank you. Adolf.

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