Phenacyl bromide → HCID 9995534, compound

HRID 720412Notes

Reaction equation

HRID 720412 reaction equation
[Br-].[CH3:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N+:10]2[CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:5][CH:4]=1.BrCC(C1C=CC=CC=1)=O.CC1C=C2C([CH:37]=[CH:38][CH:39]=[N:40]2)=CC=1>C(#N)C>[C:14]([C:13]1[N:10]2[C:11]3[C:6]([CH:7]=[CH:8][C:9]2=[C:38]([C:39]#[N:40])[CH:37]=1)=[CH:5][CH:4]=[C:3]([CH3:2])[CH:12]=3)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 119277-MethylquinolineHCID 21892112HCID 21892112, compound

Product 1

HCID 9995534HCID 9995534, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Methyl-1-phenacyl-quinolinium bromide: The title compound was prepared from 2-bromo-1-phenyl-ethanone (490 mg, 2.46 mmol), 7-methyl-quinoline (302 mg, 2.11 mmol) and acetonitrile (5 mL), similar to Example 1a, and yielded 499 mg (69%) as a light tan solid: 1H NMR (CD3OD) 9.28–9.25 (m, 2H), 8.37 (d, J=8.4 Hz, 1H), 8.23–8.19 (m, 2H), 8.13–8.08 (m, 2H), 7.91 (dd, J=0.9, 8.7 Hz, 1H), 7.83–7.78 (m, 1H), 7.70–7.64 (m, 2H), 2.67 (s, 3H).

Workup

  1. customyielded 499 mg (69%) as a light tan solid

Sources & evidence

ORD record
ord-4658bf12fcc04e70972913be5a086fe6
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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