Water → HCID 20094815, compound

HRID 274064Notes

Reaction equation

HRID 274064 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1)([O-])=O.[Cl-].[NH4+].O>[Fe].C(O)C>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 18007286HCID 18007286, compound

Product 1

HCID 20094815HCID 20094815, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (0.20 g), iron powder (218 mg), ammonium chloride (52 mg), water (1.2 ml) and ethanol (4 ml) was refluxed for 2 hours. After cooling, the insoluble material was filtered off and the filtrate was evaporated in vacuo. To the residue was added ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform as an eluent to give 3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (153 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe insoluble material was filtered off
  4. customthe filtrate was evaporated in vacuo
  5. additionTo the residue was added ethyl acetate and water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel with chloroform as an eluent

Sources & evidence

ORD record
ord-f2e0b6d900fd4528a3b7eb814e9b8443
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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