Benzyl Bromide → 1-benzyl-4-methyl-9H-indeno[2,1-b]pyridinium bromide

HRID 2272012Notes

Reaction equation

HRID 2272012 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:3]=12.[CH2:15]([Br:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O>[Br-:22].[CH2:15]([N+:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:8][C:4]=12)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 125062784-methyl-9H-indeno[2,1-b]pyridine

Product 1

HCID 671942071-benzyl-4-methyl-9H-indeno[2,1-b]pyridinium bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-methyl-9H-indeno[2,1-b]pyridine (0.64 g) and benzyl bromide (0.42 mL) in acetone (5 mL) is stirred at reflux temperature for 4 h. After cooling to room temperature, the precipitate is separated by filtration, washed with little diethyl ether, and dried to give the title compound as a beige solid. Yield: 0.93 g (75% of theory); LC (method 1): tR=2.49 min; Mass spectrum (ESI+): m/z=272 [M−Br]+.

Workup

  1. temperatureat reflux temperature for 4 h
  2. customthe precipitate is separated by filtration
  3. washwashed with little diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-bc1c41261d464d208f9b4b7d78ef3645
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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