Stannous Chloride → HCID 11543545, compound

HRID 418816Notes

Reaction equation

HRID 418816 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[O:19])[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:5]([N+:20]([O-])=O)[CH:4]=1.Cl[Sn]Cl>C(O)C.O>[NH2:20][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:9]1[O:10][C:11]2[C:16]([C:17](=[O:19])[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 11637961HCID 11637961, compound

Product 1

HCID 11543545HCID 11543545, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(4-Methoxy-2-nitrophenyl)-4H-chromen-4-one (1.5 g, 5.04 mmol) was dissolved in ethanol (30 mL) and heated at reflux. SnCl2 (4.97 g , 26.23 mmol) was added. The mixture was heated under reflux for 20 min. The reaction mixture was cooled to rt diluted with water, neutralized and extracted with ethyl acetate to give the crude compound. This was purified by column chromatography using 3% MeOH in CH2Cl2 to give 2-(2-amino-4-methoxyphenyl)-4H-chromen-4-one (790 mg, 58%).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 20 min
  5. extractionextracted with ethyl acetate
  6. customto give the crude compound
  7. customThis was purified by column chromatography

Sources & evidence

ORD record
ord-01d42f20cccd4437a68114c260216502
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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