HCID 19864646, compound → HCID 19864641, compound

HRID 1200109Notes

Reaction equation

HRID 1200109 reaction equation
[OH:1][C:2]1([CH2:17]N)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[CH2:3]1>O.C(O)(=O)C>[CH:13]1[C:5]2[O:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH2:17][C:2](=[O:1])[CH2:3][C:4]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 19864646HCID 19864646, compound

Product 1

HCID 19864641HCID 19864641, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

10,11-Dihydro-10-hydroxy-dibenz[b,f]oxepine-10-methanamine (46.6 g - as prepared in example A) was dissolved in a mixture of water (940 ml) and acetic acid (23 ml), and the solution was filtered and cooled below 5° C. To this cooled solution was quickly added a solution of sodium nitrite (20.5 g) in the minimum of water, the cooling was then removed, and the mixture was allowed to stand at ambient temperature for eighteen hours. The product was filtered, dissolved in dichloromethane, and the solution was filtered through silica, then evaporated. The residue was crystallised from 1,1'-oxybisethane/n-hexane to give pure 5H-dibenz[b,g]oxocin-6(7H)-one (34 g). M.P. 86° C. (Lit. 84.5° C. J.Org.Chem.34.1165(1969).

Workup

  1. filtrationthe solution was filtered
  2. temperaturecooled below 5° C
  3. additionTo this cooled solution was quickly added a solution of sodium nitrite (20.5 g) in the minimum of water
  4. customthe cooling was then removed
  5. waitto stand at ambient temperature for eighteen hours
  6. filtrationThe product was filtered
  7. dissolutiondissolved in dichloromethane
  8. filtrationthe solution was filtered through silica
  9. customevaporated
  10. customThe residue was crystallised from 1,1'-oxybisethane/n-hexane

Sources & evidence

ORD record
ord-c6be9fed82bd44fb91a207376e404677
Source dataset
uspto-grants-1990_02
Patent number
US04904688

Reaction notes

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