Synthesis of 2-aminoquinoline

Preparation of 2-aminoquinoline

Preparation of 2-aminoquinoline

Preparation of 2-aminoquinoline

Two molar equivalents of sodium amide are suspended in boiling xylene and one molar equivalent of quinoline is added. The mixture is heated to reflux until the rate of hydrogen evolution is low (approximately 1 hour). The cold reaction mixture is hydrolyzed by the cautious addition of excess water, and the xylene layer is separated and extracted with concentrated hydrochloric acid. The acid extracts are treated with excess sodium hydroxide and extracted with ether. The combined ethereal extracts and xylene layer are distilled, and the fraction boiling around 200°/30 mm. is recrystallized from toluene. The yield is 32% of white needles, m.p. 130°.

Ind. Eng. Chem., 32, 177 (1940).

IUPAC Name

quinolin-2-amine

InChI

InChI=1S/C9H8N2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H,(H2,10,11)

InChI Key

GCMNJUJAKQGROZ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C=CC(=N2)N

Depositor-Supplied Synonyms

2-AMINOQUINOLINE, quinolin-2-amine, 580-22-3, 2-Quinolinamine, Quinoline, 2-amino-, Aminoquinoline, Quinolinamine, quinolin-2-ylamine, 2-1H-QUINOLINIMINE, CHEMBL61236, 2-quinolylamine, CCRIS 1677, GCMNJUJAKQGROZ-UHFFFAOYSA-N, EINECS 209-458-8, NSC 57739, NSC 58387, BRN 0113163, 101772-05-8, 31135-62-3, AC-907/25014242, amino quinoline, 2ohl, 2-amino-quinoline, quinoline-2-amine, Fragment 19, 2-Aminoquinoline 1, PubChem5818, ACMC-1AH5U, AC1L1X8D, SCHEMBL38775, KSC223A9P, AC1Q531G, SCHEMBL1146984, BDBM14322, CTK1C3097, CTK4C1715, MolPort-000-141-995, HMS1719H05, Quinolin-2-amine; 2-Quinolinamine, ACT03947, NSC57739, NSC58387, ANW-32862, CA-077, NSC-57739, NSC-58387, SBB051994, WTI-10498, ZINC19074717, AKOS000279069, MCULE-9057285409, PS-4207, RP01417, RTC-062228, TRA0162779, VQ10090, NCGC00188269-01, AC-13271, AJ-70794, AK-26798, AN-46067, BC205864, BR-26798, HE000833, HE241239, KB-20837, L197, AB1003948, DB-005975, fragment 2 (J. med. chem.,50,1116), KB-175907, LS-141297, ST2409595, TC-062228, WT-130355, A0417, A8247, AM20061864, FT-0081421, FT-0632430, ST50409632, EN300-10204, S-1912, 22860-EP2286812A1, 22860-EP2295421A1, 22860-EP2308848A1, 22860-EP2315502A1, 22860-EP2371810A1, 22860-EP2371812A1, 5-22-10-00220 (Beilstein Handbook Reference), A831703, J-400243, T5290634, 3B3-005232, 139265-95-5, 2AQ

Removed Synonyms

CID11379

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