Stannous Chloride → 5-(3-Aminophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

HRID 1069082Notes

Reaction equation

HRID 1069082 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)[CH:6]=1)=[O:4].[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 545606555-(3-Nitrophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

Product 1

HCID 697796895-(3-Aminophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl esterYield 80.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Nitrophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester (650 mg) and tin(II) chloride (2.3 g) in ethyl acetate (28 mL) were heated at 70° C. for 16 h. The mixture was allowed to cool and poured onto ice. The pH was adjusted to 7-8 by addition of saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, treated with charcoal and dried over sodium sulfate. Filtration and removal of solvent afforded the title compound as an oil (470 mg). Electrospray MS (positive ion): (M+H) 270.4.

Workup

  1. temperatureto cool
  2. additionpoured onto ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. additiontreated with charcoal
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-5718ecf11b0a46a3b4f1f8314bd2d881
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

Loading…