Synthesis of 4-(bromomethyl)quinoline

Preparation of 4-(bromomethyl)quinoline

Preparation of 4-(bromomethyl)quinoline

Preparation of 4-(bromomethyl)quinoline

0.1 mole of 4-methylquinoline (lepidine) is added to a stirred suspension of N-bromosuccinimide (0.08 mole) in carbon tetrachloride at 60° C. The mixture is boiled under reflux for 30 min, then filtered hot. The 4-(bromomethyl)quinoline crystallizes from the filtrate in white crystals (10 g), from which adhering succinimide is removed by thorough washing with water. When dried in a vacuum, 4-(bromomethyl)quinoline has m.p. 88-91°. 4-(Bromomethyl)quinoline is unstable and should be used as soon as possible.

J. Amer. Chem. Soc, 71, 2906 (1949).

IUPAC Name

4-(bromomethyl)quinoline

InChI

InChI=1S/C10H8BrN/c11-7-8-5-6-12-10-4-2-1-3-9(8)10/h1-6H,7H2

InChI Key

QJQXVPCIRZUOIP-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

4-(bromomethyl)quinoline, 5632-16-6, 4-BROMOMETHYL-QUINOLINE, (4-bromomethyl)quinoline, 4-BROMOMETHYLQUINOLINE, SCHEMBL2592802, CTK5A4975, MolPort-020-642-819, 8238AB, ANW-63739, ZINC36426822, AKOS013180950, AJ-92810, AK-68767, HE101177, SC-12798, SY031349, DB-072132, KB-238870, TC-152484, Z-6763

Removed Synonyms

C10H8BrN, CID11775705

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