Quinoline → HCID 10807217, compound

HRID 1160089Notes

Reaction equation

HRID 1160089 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.[Br:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=[O:14]>ClC(Cl)C>[Br-:11].[O:14]=[C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[CH2:12][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 692722-Bromo-4'-methylacetophenone

Product 1

HCID 10807217HCID 10807217, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of quinoline (931 μl, 7.72 mmol) and 2-bromo-4′-methyl-acetophenone (1.828 g, 7.71 mmol) in dichloroethane (6 mL) was refluxed for 1 hour. The resulting brown paste was triturated with ether and filtered. After recristallization from methanol the product was isolated in 46% yield: mp 230-233° C.; 1H NMR 500 MHz (DMSO-d6) δ 2.45 (s, 3H), 7.02 (s, 2H), 7.49 (d, 2H, J=7.9 Hz), 8.05 (d, 3H, J=7.9 Hz), 8.21 (m, 1H), 8.32 (dd, 1H, J=6.1, 7.9 Hz), 8.41 (d, 1H, J=9.2 Hz), 8.55 (d, 1H, J=8.2 Hz), 9.45 (d, 1H, J=8.2 Hz), 9.56 (d, 1H, J=5.5 Hz); Elem. anal. found: C, 63.00; H, 4.77; N, 4.09% (calcd for C18H16BrNO: C, 63.17; H, 4.71; N, 4.09%).

Workup

  1. customThe resulting brown paste was triturated with ether
  2. filtrationfiltered
  3. customAfter recristallization from methanol the product was isolated in 46% yield

Sources & evidence

ORD record
ord-e1da11b80d8a46cabc3abe9d5ce08dfc
Source dataset
uspto-grants-2010_10
Patent number
US07816352B2

Reaction notes

Loading…