Phenacyl bromide → HCID 10425501, compound

HRID 720410

Reaction equation

HRID 720410 reaction equation
[Br-].[CH3:2][C:3]1[CH:4]=[N+:5]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.BrCC(C1C=CC=CC=1)=O.[CH3:32][C:33]1[CH:34]=[N:35]C2C(C=1)=CC=CC=2>C(#N)C>[C:14]([C:13]1[N:5]2[C:6]3[C:11]([CH:12]=[C:3]([CH3:2])[C:4]2=[C:33]([C:34]#[N:35])[CH:32]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 119263-MethylquinolineHCID 21892121HCID 21892121, compound

Product 1

HCID 10425501HCID 10425501, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Methyl-1-phenacyl-quinolinium bromide: The title compound was prepared from 2-bromo-1-phenyl-ethanone (481 mg, 2.405 mmol), 3-methyl-quinoline (296 mg, 2.08 mmol) and acetonitrile (5 mL), similar to Example 1a, and yielded 640 mg (89%) as an off white solid: 1H NMR (CDCl3) 0.38 (d, J=1.8 Hz, 1H), 8.74 (s, 1H), 8.31 (m, 1H), 8.28 (m, 1H), 8.17 (dd, J=1.5, 8.4 Hz, 1H), 8.01 (m, 1H), 7.94–7.87 (m, 2H), 7.71 (m, 1H), 7.57 (t, J=7.8 Hz, 2H), 7.49 (s, 2H), 2.81 (s, 3H).

Workup

  1. customyielded 640 mg (89%) as an off white solid

Sources & evidence

ORD record
ord-75840e5472614453991df0df02d35f8d
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Linked notes

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