Ethanol → HCID 18334159, compound

HRID 2269421Notes

Reaction equation

HRID 2269421 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)[NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(O)C.[Sn](Cl)[Cl:32].[OH-].[Na+]>Cl.C(OCC)(=O)C>[ClH:32].[NH2:25][C:21]1[CH:20]=[C:19]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 18334174HCID 18334174, compound

Product 1

HCID 18334159HCID 18334159, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]benzamide (3.24 g) [prepared as described in step (c) above] was added in small portions to a 1:1 by volume mixture of ethanol and concentrated hydrochloric acid at ambient temperature. Tin (II) chloride (6.78 g) was then added in small portions to the mixture in an ice bath. The mixture was stirred at ambient temperature for 20 minutes and then heated under reflux for 2 hours. After cooling, the reaction mixture was neutralized with aqueous solution of sodium hydroxide and the insoluble material was removed by filtration using a Celite (trade mark) filter aid. The filtrate was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 2:1 by volume mixture of hexane and ethyl acetate as the eluant, to afford a colorless oil. This oil was dissolved in a solution of hydrogen chloride in ethyl acetate (4N) and the solvent was evaporated to dryness. The residual solid was suspended in diethyl ether and filtered, to afford the title compound (2.68 g) as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe insoluble material was removed by filtration
  5. filtrationfilter aid
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customThe residue was purified by chromatography through a silica gel column
  11. additionby volume mixture of hexane and ethyl acetate as the eluant
  12. customto afford a colorless oil
  13. customthe solvent was evaporated to dryness
  14. filtrationfiltered

Sources & evidence

ORD record
ord-11f056ab06544e748a7c82a58388a484
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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