Diethyl Ether → 2-(4-Phenylbenzoylmethyl)imidazo [3,4-a]pyridinium Bromide

HRID 894056Notes

Reaction equation

HRID 894056 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.CCOCC.[C:15]1([C:21]2[CH:30]=[CH:29][C:24]([C:25](=[O:28])[CH2:26][Br:27])=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[Br-:27].[C:15]1([C:21]2[CH:22]=[CH:23][C:24]([C:25]([CH2:26][N+:2]3[CH:1]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]4[CH:3]=3)=[O:28])=[CH:29][CH:30]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 274090Imidazo(1,5-a)pyridine

Product 1

HCID 128971102-(4-Phenylbenzoylmethyl)imidazo [3,4-a]pyridinium Bromide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazo[3,4-a]pyridine (7.1 g., 60 mmoles), dissolved in 150 ml. of ether, was mixed with p-phenylphenacyl bromide dissolved in 100 ml. of tetrahydrofuran and stirred for 4 hours at room temperature. A first crop of crystalline 2-(4-phenylbenzoylmethyl)imidazo[3,4-a]pyridinium bromide [7.8 g., m.p. 258°-260° C. (dec.)] was recovered by filtration. After standing four days at room temperature, a second crop of crystallized product [9.5 g., m.p. 262°-264° C. (dec.)] was recovered from the filtrate.

Workup

  1. dissolutiondissolved in 100 ml
  2. filtrationA first crop of crystalline 2-(4-phenylbenzoylmethyl)imidazo[3,4-a]pyridinium bromide [7.8 g., m.p. 258°-260° C. (dec.)] was recovered by filtration
  3. customa second crop of crystallized product [9.5 g., m.p. 262°-264° C. (dec.)] was recovered from the filtrate

Sources & evidence

ORD record
ord-c7aadcbd0fd24ea8ac4702d91700ad5d
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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