N-bromobutanimide → 8-(Bromomethyl)-7-chloroquinoline

HRID 1388529Notes

Reaction equation

HRID 1388529 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C1C=CC=CC=1>[Cl:1][C:2]1[C:11]([CH2:12][Br:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 130907837-Chloro-8-methylquinoline

Product 1

HCID 131521968-(Bromomethyl)-7-chloroquinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7-Chloro-8-methylquinoline (1 g.) [Bradford et al., J. Chem. Soc., p. 437 (1947)] is dissolved in 20 ml. of benzene and brominated with one equivalent of N-bromosuccinimide in the presence of catalytic amounts of peroxide. The product, 7-chloro-8-(bromomethyl)-quinoline is isolated by evaporation.

Sources & evidence

ORD record
ord-fbf720a547bf425bb076c2186876b500
Source dataset
uspto-grants-1984_02
Patent number
US04431810

Reaction notes

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