Sulfuric Acid → HCID 3046885, compound

HRID 372557Notes

Reaction equation

HRID 372557 reaction equation
S(=O)(=O)(O)O.[CH2:6]([NH:9][CH:10]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[CH:12](O)[CH2:11]1)[CH:7]=[CH2:8]>O1CCOCC1>[CH2:6]([NH:9][CH:10]1[CH:11]=[CH:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][CH2:16]1)[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 53686665HCID 53686665, compound

Product 1

HCID 3046885HCID 3046885, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12.4 ml of 18 N sulfuric acid were added to a refluxing solution of 6.2 g of 7-allylamino-5-ξ-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene in 124 ml of dioxane and the mixture was refluxed for 30 minutes and was cooled. The mixture was concentrated to 40 ml and 100 ml of ice water were added. The aqueous phase was washed with ethyl acetate and made alkaline with concentrated ammonium hydroxide. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness to obtain 4.5 g of 7-allylamino-6,7-dihydro [5H] benzocycloheptene.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. temperaturewas cooled
  3. concentrationThe mixture was concentrated to 40 ml and 100 ml of ice water
  4. additionwere added
  5. washThe aqueous phase was washed with ethyl acetate
  6. extractionThe mixture was extracted with methylene chloride
  7. washthe organic phase was washed with water
  8. customdried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-a7425d6fd1fe4171ac207ed3115a6cd6
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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