Water → HCID 15512538, compound

HRID 2299182Notes

Reaction equation

HRID 2299182 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[O:8][C:9]3[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([OH:19])[C:10]=3[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1)([O-])=O.[Sn](Cl)Cl.O>C(O)C.O1CCOCC1>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]2[O:8][C:9]3[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([OH:19])[C:10]=3[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 15512537HCID 15512537, compound

Product 1

HCID 15512538HCID 15512538, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1.40 g of 2-nitro-7,9-dihydroxy-10,11-dihydrodibenz[b,f]oxepin-10,11 -one (Compound 70) and 4.40 g of tin (II) chloride.2H2O were suspended in 20 ml of ethanol and 20 ml of 1,4-dioxane, followed by reflux under heating for 3 hours. Water was added to the reaction solution, which was then extracted in ethyl acetate. The extracted solution was sequentially washed in water and then an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by silica gel column chromatography (elution solvent; dichloromethane:methanol=95:5), to recover the entitled Compound 71 represented by the formula (0.64 g; yield of 51%). The melting point of the amorphous powder recovered by recrystallization in hexane and ethyl acetate was 227-229° C.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 3 hours
  3. extractionwas then extracted in ethyl acetate
  4. washThe extracted solution was sequentially washed in water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by silica gel column chromatography (elution solvent; dichloromethane:methanol=95:5)
  8. customto recover the entitled Compound 71
  9. customThe melting point of the amorphous powder recovered by recrystallization in hexane
  10. customwas 227-229° C.

Sources & evidence

ORD record
ord-463dd2077dce48b2a7016e532d041b0f
Source dataset
uspto-grants-2002_12
Patent number
US06495592B1

Reaction notes

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