Water → HCID 3046875, compound

HRID 372551Notes

Reaction equation

HRID 372551 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[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(O)[CH2:9]1.O>O1CCOCC1>[CH3:6][NH:7][CH:8]1[CH:9]=[C:10]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 19789815HCID 19789815, compound

Product 1

HCID 3046875HCID 3046875, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9.2 ml of 18 N sulfuric acid were added to a refluxing solution of 4.62 g of the product of Step A in 90 ml of dioxane and the mixture was refluxed for 15 minutes and was then cooled. The mixture was poured into iced water and was extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 2-8-1 benzene-ethyl acetate-triethylamine mixture and then a 95-5-1 chloroform-methanol-triethylamine mixture to obtain 3.3 g of 7-methylamino-9-phenyl-6,7-dihydro [5H] benzocycloheptene.

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperaturewas then 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. washwas eluted with a 2-8-1 benzene-ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-5647d04c62a144d0917b136f276b66e2
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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