Synthesis of 2-methylindole

Preparation of 2-methylindole

Preparation of 2-methylindole

Preparation of 2-methylindole

30 g phenylhydrazine are mixed wih 18 g acetone. The mixture becomes very warm and a good deal of water separates. The mixture is heated on a water bath for 15 minutes, a small portion being occasionally tested with Fehling’s solution. As long as phenylhydrazine is present in excess, the Fehling’s solution is reduced; more acetone is then added from time to time until the reducing action of the mixture has almost ceased. The turbid oil (crude acetone-phenylhydrazone) is placed in a large copper crucible, and the excess of acetone removed by heating on a water bath for 30 minutes. 200 g of dry zinc chloride are next added, and the mixture heated on the bath with frequent stirring. The whole is then heated on an oil bath to 180° C, and, when in a few minutes the mass has acquired a dak colour, the cucible is immediately removed from the bath and stirred. The reaction is complete in a short time, and can be followed by the change in colour of the fusion and the evolution of vapours. The dark fused mass is treated with 3½ times its weight of hot water, and distilled in steam after acidification with a little hydrochloric acid. The 2-methylindole distils over, slowly but completely, as a pale yellow oil which soon solidifies. This is filtered off, melted to free it from water and distilled. It must be kept in a well-closed bottle. The yield of 2-methylindole is 55%; Pale yellow crystals; obnoxious odour; m.p. 59° C; b.p. 272° C/750 mmHg.

Systematic organic chemistry, by W. M. Cumming, 169-170, 1937.





InChI Key


Canonical SMILES


MeSH Synonyms

2-methylindole, 2-methylindole sodium salt

Depositor-Supplied Synonyms

2-METHYLINDOLE, 2-Methyl-1H-indole, 95-20-5, 1H-Indole, 2-methyl-, Indole, 2-methyl-, 2-METHYL INDOLE, CHEBI:49402, BHNHHSOHWZKFOX-UHFFFAOYSA-N, NSC 7514, EINECS 202-398-3, F0290-0682, AI3-03945, Methylketole, methyl indole, 2-methylindol, 2-methyl-indole, PubChem7504, 2-methyl-1-H-indole, ACMC-209rxz, AC1L1OAA, SCHEMBL12420, M51407_ALDRICH, KSC486Q8R, Indole, 2-methyl- (8CI), SCHEMBL377807, UNII-I7CN58827I, ARONIS020142, CHEMBL259419, CTK3I6888, NSC7514, MolPort-000-157-236, I7CN58827I, KUC106612N, ACT07545, KSC-09-215A, NSC-7514, STR01200, ZINC1088076, AC-611, ANW-40485, SBB058480, STK044221, ZINC01088076, AKOS000119568, CG-0500, MCULE-9033876547, RP19965, RTC-066332, VI30173, TRA-0184593, AJ-25013, AK-44448, AN-15673, BC200996, BR-44448, CJ-04762, HE009180, KB-25194, LS-83246, LS-83247, SC-07430, SC-25318, ST040425, ZB016000, DB-031753, KB-231714, TC-066332, TL8005985, FT-0612877, FT-0613057, M0346, ST24032510, A11136, M-3895, M-5887, AB00375786-04, S10-0022, T7100940, 3B3-020035, InChI=1/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H, 2MI

Removed Synonyms

BENZOXAZOLE, 2-METHYL-, CID7224, 1-Chloro-3,5-dimethoxy-2-nitrobenzene, 90-25-5, 95-21-6

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