HCID 75005637, compound → HCID 90795739, compound

HRID 436605Notes

Reaction equation

HRID 436605 reaction equation
[OH:1][CH:2]1[CH:8]2[NH:9][CH:5]([C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=32)[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2>[Si]([O-])([O-])([O-])[O-].[Ag+].[Ag+].[Ag+].[Ag+].C1C=CC=CC=1>[NH:9]1[CH:8]2[C:2](=[O:1])[C:3]3[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=3[CH:5]1[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=12

Participants

4

Reactant 1

HCID 75005637HCID 75005637, compound

Product 1

HCID 90795739HCID 90795739, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 86733097HCID 86733097, compoundCatalyst2×HCID 241BenzeneSolvent

Procedure

A mixture of 1.5 g of 11-hydroxy-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d) cycloheptene dl cis, 60 ml of benzene and 3 g of silver silicate was refluxed with stirring for 45 minutes and then 1.5 g of silver silicate were added and reflux was continued for another hour. The mixture was filtered hot and the filter was washed with methylene chloride. The combined filtrates were washed with 2N hydrochloric acid and the acid phase was made alkaline with sodium hydroxide. The mixture was extracted with methylene chloride and the organic phase was dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with a 95-5 mixture of chloroform-methanol to obtain 780 mg of 10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d) cycloheptene-11-one dl melting at 100° C identical to that of Example 1.

Workup

  1. temperaturewas refluxed
  2. temperaturereflux
  3. waitwas continued for another hour
  4. filtrationThe mixture was filtered hot
  5. washthe filter was washed with methylene chloride
  6. washThe combined filtrates were washed with 2N hydrochloric acid
  7. extractionThe mixture was extracted with methylene chloride
  8. dry with materialthe organic phase was dried over magnesium sulfate
  9. distillationdistilled to dryness under reduced pressure
  10. customThe residue was chromatographed over silica gel
  11. washeluted with a 95-5 mixture of chloroform-methanol

Sources & evidence

ORD record
ord-924d2451c8ec4d4386cd686cec77c691
Source dataset
uspto-grants-1977_02
Patent number
US04009273

Reaction notes

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