Reaction #807593

ord-92a7b795d83843ec92d0c6328e2ba3d6

Reaction equation

O=C(C[n+]1cccc2cc(Cl)ccc21)c1ccccc1.[Br-]
6-Chloro-1-phenacyl-quinolinium bromide
O=C(CBr)c1ccccc1
2-bromo-1-phenyl-ethanone
Clc1ccc2ncccc2c1
6-chloro-quinoline
N#Cc1cc(C(=O)c2ccccc2)n2c1ccc1cc(Cl)ccc12
title compound
N#Cc1cc(C(=O)c2ccccc2)n2c1ccc1cc(Cl)ccc12
1-Benzoyl-7-chloro-3-cyano-pyrrolo[1,2-a]quinoline

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otheryielded 433 mg (63%) as an off white solid

Procedure

6-Chloro-1-phenacyl-quinolinium bromide: The title compound was prepared from 2-bromo-1-phenyl-ethanone (483 mg, 2.43 mmol), 6-chloro-quinoline (312 mg, 1.91 mmol) and acetonitrile (5 mL), similar to Example 1a, and yielded 433 mg (63%) as an off white solid: 1H NMR (CDCl3) 10.40 (d, J=5.7 Hz, 1H), 8.95 (d, J=8.7 Hz, 1H), 8.31 (m, 1H), 8.29 (m 1H), 8.24 (d, J=2.1 Hz, 1H), 8.19–8.14 (m, 2H), 7.99 (dd, J=2.1, 9.3 Hz, 1H), 7.70–7.65 (m, 3H), 7.53 (t, J=7.8 Hz, 2H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07135480B2uspto-grants-2006_11