Pyridine → HCID 86743951, compound

HRID 1651075Notes

Reaction equation

HRID 1651075 reaction equation
O=[C:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH2:3]1.Cl.[NH2:19][OH:20].N1C=CC=CC=1>C(O)C>[OH:20][N:19]=[C:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 283964HCID 283964, compoundHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86743951HCID 86743951, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-oxo-dibenzo[a,e]cyclooctene (1 g, Example 1, step E) in ethanol (40 ml) was added hydroxylamine hydrochloride (0.316 g) and pyridine (0.404 ml). This mixture was heated to reflux for 8hr, cooled to room temperature and evaporated to dryness. To the residue was added ethyl acetate (100 ml). water (100 ml),then sodium hydroxide (1M) until pH 10. The aqueous layer was extracted with ethyl acetate (200 ml), the combined organic layers were washed with water (100 ml), brine (100 ml) then dried and evaporated to yield the crude product. Recrystallisation from ethyl acetate-hexane gave pure 5-hydroxyimino-dibenzo[a,e]cyclooctene (0.72 g, m.p. 191°-192°C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 8hr
  3. customevaporated to dryness
  4. additionTo the residue was added ethyl acetate (100 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (200 ml)
  6. washthe combined organic layers were washed with water (100 ml), brine (100 ml)
  7. customthen dried
  8. customevaporated
  9. customto yield the crude product
  10. customRecrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2e6ee9beb1514f1b8695b83d65bda6cc
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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