2-bromo-1-[4-(diethylamino)phenyl]ethanone → HCID 21892170, compound

HRID 720418Notes

Reaction equation

HRID 720418 reaction equation
[Br-].[CH2:2]([N:4]([CH2:24][CH3:25])[C:5]1[CH:23]=[CH:22][C:8]([C:9](=[O:21])[CH2:10][N+:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].BrCC(C1C=C[C:33]([N:36](CC)CC)=[CH:32][CH:31]=1)=O>>[C:33]([C:32]1[CH:31]=[C:10]([C:9](=[O:21])[C:8]2[CH:7]=[CH:6][C:5]([N:4]([CH2:2][CH3:3])[CH2:24][CH3:25])=[CH:23][CH:22]=2)[N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=12)#[N:36]

Participants

3

Reactant 2

HCID 27950302-bromo-1-[4-(diethylamino)phenyl]ethanoneHCID 21892126HCID 21892126, compound

Product 1

HCID 21892170HCID 21892170, compound

Procedure

1-(4-Diethylamino-phenacyl)-quinolinium bromide: The title compound was prepared from 2-bromo-1-(4-diethylamino phenyl) ethanone (2.23 g, 13.6 mmol), by a method similar to that described for the preparation of Example 1a, and yielded 1.67 g (92%). 1H NMR (DMSO-d6): 9.60 (d, J=6.0 Hz, 1H), 9.52 (d, J=8.4 Hz, 1H), 8.64 (d, J=8.1 Hz, 1H), 8.41 (d, J=9.9 Hz, 1H), 8.39 (d, J=7.5 Hz, 1H), 8.31 (t, J=6.9 Hz, 1H), 8.14 (dd, J=7.8, 6.9 Hz, 1H), 8.04, (d, J=8.7 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.93 (s, 2H), 3.60 (q, J=8.4 Hz, 4H), 1.26 (t, J=6.6 Hz, 6H).

Workup

  1. customthat described for the preparation of Example 1a
  2. customyielded 1.67 g (92%)

Sources & evidence

ORD record
ord-f88f8f04007941abb7d74ba40e05839f
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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