Quinoline → HCID 86624613, compound

HRID 1160088Notes

Reaction equation

HRID 1160088 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][N:13]=[C:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[CH2:15][Br:16]>CC(C)=O>[Br-:16].[CH3:11][O:12][N:13]=[C:14]([C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)[CH2:15][N+:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 86049356HCID 86049356, compound

Product 1

HCID 86624613HCID 86624613, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of quinoline and 2-bromo-1-p-tolylethanone O-methyl oxime was stirred refluxed in acetone for 5 days. A precipitate was separated by filtration and rinsed with Et2O to give a light orange solid in 11% yield: mp 285-288° C.; 1H NMR 500 MHz (DMSO-d6) δ 2.19 (s, 3H), 4.06 (s, 3H), 6.46 (s, 2H), 7.08 (d, 2H, J=7.9 Hz), 7.37 (d, 2H, J=8.2 Hz), 8.04 (t, 1H, J=7.3 Hz), 8.17 (m, 1H), 8.22 (d, 1H, J=9.2 Hz), 8.32 (m, 1H), 8.44 (d, 1H, J=7.9 Hz), 9.68 (d, 1H, J=8.2 Hz), 9.28 (d, 1H, J=5.8 Hz); Elem. anal. found: C, 61.17; H, 5.18; N, 7.50% (calcd for C19H19BrN2O: C, 61.47; H, 5.16; N, 7.55%).

Workup

  1. customA precipitate was separated by filtration
  2. washrinsed with Et2O
  3. customto give a light orange solid in 11% yield

Sources & evidence

ORD record
ord-57a31b9aa93a42debfca0f34ad3f0de2
Source dataset
uspto-grants-2010_10
Patent number
US07816352B2

Reaction notes

Loading…