Synthesis of 6-aminoquinoline

Preparation of 6-aminoquinoline

Preparation of 6-aminoquinoline

Preparation of 6-aminoquinoline

500 ml of water is added to a solution of 100 g. of 6-nitroquinoline in 500 ml. of glacial acetic acid, and to the resulting solution 80 g. of iron powder is added slowly with stirring at 60°. After reduction is complete, the mixture is cooled and made alkaline by the addition with stirring of solid sodium carbonate. After thorough cooling the precipitated solid is removed by filtration, dried, powdered, and extracted repeatedly and thoroughly with boiling ether. The combined extracts are dried over sodium sulfate, and the solvent is evaporated. The residue is distilled to give 70 g. (85%) of 6-aminoquinoline, b.p. 187-200°/10-13 mm., m.p. 114°.

J. Am. Chem. Soc., 68, 874 (1946).

IUPAC Name

quinolin-6-amine

InChI

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

InChI Key

RJSRSRITMWVIQT-UHFFFAOYSA-N

Canonical SMILES

C1=CC2=C(C=CC(=C2)N)N=C1

MeSH Synonyms

6-aminoquinoline

Depositor-Supplied Synonyms

6-AMINOQUINOLINE, Quinolin-6-amine, 580-15-4, 6-Quinolinamine, Quinoline, 6-amino-, Quinolin-6-ylamine, 6-quinolylamine, MLS000080747, CCRIS 1681, RJSRSRITMWVIQT-UHFFFAOYSA-N, EINECS 209-453-0, NSC 58388, SMR000036663, 6 aminoquinoline, 3kqp, 6-Amino-quinoline, AC1L1X7V, AC1Q52DW, ACMC-1B07C, cid_11373, KSC271K6R, BIDD:GT0636, CHEMBL99408, SCHEMBL160217, Quinoline, 6-amino- (8CI), 275581_ALDRICH, AC1Q52G6, STOCK1S-56723, 07342_FLUKA, BDBM32026, CTK1H1568, MolPort-000-140-070, HMS2451C16, ZINC163693, ACT08277, NSC58388, ANW-32857, CA-856, NSC-58388, SBB004130, STK328120, WTI-11341, ZINC00163693, AKOS000131287, AC-4708, LS20703, MCULE-1252717566, PS-4529, RP01415, RTC-040338, TRA0001156, VQ10285, AJ-16065, AK-29433, AN-11727, BR-29433, CJ-02100, HE019929, KB-44648, Q975, ZB008028, AB0017922, AB1007162, DB-031615, KB-259642, LS-188156, TC-040338, WT-130064, AM20061341, BB 0221206, FT-0620944, ST24029617, ST50532774, EN300-41836, A18930, M-3271, US8546389, 98, AC-907/25014243, S08-0109, T6339135, W-105419, 3B3-017843, ES5

Removed Synonyms

CID11373, ethyl 4-benzylmorpholine-3-carboxylate, A1370, 2478-10-6

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