Sulfuric Acid → HCID 3046871, compound

HRID 372549Notes

Reaction equation

HRID 372549 reaction equation
S(=O)(=O)(O)O.[CH3:6][NH:7][CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH:10](O)[CH2:9]1.[OH-].[NH4+].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O1CCOCC1>[CH3:6][NH:7][CH:8]1[CH:9]=[CH:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 6097028Ammonium SulfateHCID 53954468HCID 53954468, compound

Product 1

HCID 3046871HCID 3046871, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

50 ml of 18 N sulfuric acid were added over 30 minutes to a refluxing mixture of 50 g of 7-methylamino-5-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene and 500 ml of dioxane and the mixture was refluxed for an hour and then was cooled. The pH was adjusted to 10 with concentrated ammonium hydroxide solution and the mixture was saturated with ammonium sulfate and was extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, dried and evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 95-5-2 methylene chloride-methanol-triethylamine mixture yielded 22.8 g of 7-methylamino-6,7-dihydro [5H] benzocycloheptene.

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. temperaturewas cooled
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed with aqueous sodium chloride solution
  5. customdried
  6. customevaporated to dryness
  7. customthe residue was chromatographed over silica gel
  8. washElution with a 95-5-2 methylene chloride-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-c5610795965245bd9edfec5d5ef60c37
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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