Phenacyl bromide → HCID 10044981, compound

HRID 720414Notes

Reaction equation

HRID 720414 reaction equation
[Br-].[Br: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.CC1C=C2C([CH:37]=[CH:38][CH:39]=[N:40]2)=CC=1>C(#N)C>[C:14]([C:13]1[N:5]2[C:6]3[C:11]([CH:12]=[C:3]([Br:2])[C:4]2=[C:38]([C:39]#[N:40])[CH:37]=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 119277-MethylquinolineHCID 2841003HCID 2841003, compound

Product 1

HCID 10044981HCID 10044981, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Bromo-1-phenacyl-quinolinium bromide: The title compound was prepared from 2-bromo-1-phenyl-ethanone (485 mg, 2.44 mmol), 7-methyl-quinoline (430 mg, 2.07 mmol) and acetonitrile (5 mL), similar to Example 1a, and yielded 303 mg (36%) as a light tan solid: 1H NMR (CD3OD) 9.73 (d, J=2.1 Hz, 1H), 9.65 (d, J=1.8 Hz, 1H), 8.44 (dd, J=1.2, 8.1 Hz, 1H), 8.31–8.18 (m, 4H), 8.08 (m, 1H), 7.81 (m, 1H), 6.67 (m, 2H), 6.91 (s, 2H).

Workup

  1. customyielded 303 mg (36%) as a light tan solid

Sources & evidence

ORD record
ord-0312489ba316484ea7f0603d067be36a
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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