1-Butyl-4,4'-bipyridin-1-ium dibromide → Acridine

HRID 986955Notes

Reaction equation

HRID 986955 reaction equation
BrCC1C=CC=CC=1[C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2.[Br-].C([N+]1C=CC(C2C=C[NH+]=CC=2)=CC=1)CCC.[Br-]>C(#N)C>[CH:11]1[C:10]2[C:15](=[N:16][C:17]3[C:22]([CH:9]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 229879401-Butyl-4,4'-bipyridin-1-ium dibromideHCID 22987942HCID 22987942, compound

Product 1

HCID 9215AcridineYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 9-(2-bromomethylphenyl)acridine (1-5 mmol) and 1-butyl-4,4′-bipyridinium bromide (1-5 mmol) in the ratio of 1:1 in dry acetonitrile (30-120 mL) was stirred at 50° C. for 15h. The precipitated solid thus obtained was filtered, washed with dry acetonitrile and dichloromethane to remove any unreacted starting materials. The solid was further purified by soxhlet extraction with dichloromethane to give compound of formula 1c (wherein n=1, R=—MV2+—(CH2)3—CH3, X=Br and acridine is at the ortho position) in 35-55% yield and the product was further purified by recrystallization from ethyl acetate. Similarly, the reaction of 9-(4-bromomethyl phenyl)acridine (1-5 mmol) and 1-butyl-4,4′-bipyridinium bromide (1-5 mmol) in the ratio of 1:1 in dry acetonitrile (30-120 mL) gave compound of formula 1c (wherein n=1, R=—MV2−—(CH)3—CH3, X=Br and acridine is at the para position) in 55-70% yield and the product was further purified by recrystallization from ethyl acetate.

Workup

  1. customThe precipitated solid thus obtained
  2. filtrationwas filtered
  3. washwashed with dry acetonitrile and dichloromethane
  4. customto remove
  5. customThe solid was further purified by soxhlet extraction with dichloromethane

Sources & evidence

ORD record
ord-5e843a3d26444ef98c15ce617d251968
Source dataset
uspto-grants-2003_10
Patent number
US06630481B2

Reaction notes

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