Stannous Chloride → HCID 146733, compound

HRID 1354567Notes

Reaction equation

HRID 1354567 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH:8]=[CH:9][C:10]2[C:11]3[C:16]([N:17]=[C:18]4[C:23]=2[CH:22]=[CH:21][CH:20]=[CH:19]4)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl>C(OCC)(=O)C.C(O)C>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([CH:8]=[CH:9][C:10]2[C:23]3[C:18]([N:17]=[C:16]4[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]4)=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 730989559-(4-Nitrostyryl)acridine2×

Product 1

HCID 146733HCID 146733, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 9-(4-nitrostyryl)acridine product (2.86 g, 10.0 mmol) is dissolved in ethyl acetate (250 ml) and then brought to reflux. A solution of tin(II) chloride dehydrate (9.0 g, 40 mmol) in hot ethanol (150 ml) is cooled and added to the solution of 9-(4-nitrostyryl)acridine. The mixture is reacted under reflux and with stirring for 5 hours. After cooling, the 9-(4-aminostyryl)acridine precipitates and is isolated by filtration under vacuum. The filtrate is dried by evaporation and taken up in water (500 ml) with stirring. The solution is basified (pH 13–14) with a sodium hydroxide solution. The 9-(4-aminostyryl)acridine fraction previously isolated, which contains a high proportion of tin salt, is also basified. The 9-(4-aminostyryl)acridine is separated by filtration, washed with water and dried. It is sufficiently pure for the following step.

Workup

  1. temperatureto reflux
  2. customThe mixture is reacted
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. customthe 9-(4-aminostyryl)acridine precipitates
  6. customis isolated by filtration under vacuum
  7. customThe filtrate is dried by evaporation
  8. stirringwith stirring

Sources & evidence

ORD record
ord-5699240b52254bce8e67decfb3b46acb
Source dataset
uspto-grants-2007_05
Patent number
US07223865B2

Reaction notes

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