HCID 20094804, compound → 3-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

HRID 274073Notes

Reaction equation

HRID 274073 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=O)[CH2:11][CH2:10][CH:9]([N+:14]([O-])=O)[CH2:8][C:7]=2[CH:17]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH:9]([NH2:14])[CH2:8][C:7]=2[CH:17]=1

Participants

5

Reactant 2

HCID 20094804HCID 20094804, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 180073203-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amineYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-methoxy-8-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (0.20 g) in acetic acid (2 ml) was hydrogenated at 4 atm hydrogen atmosphere over 10% palladium on carbon (0.20 g). After removing the catalyst, the pH of the solution was adjusted to 12 with sodium hydroxide solution and the solution was extracted with ethyl acetate. The extract was washed with brine, dried over potassium carbonate, and evaporated in vacuo to give 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (153 mg).

Workup

  1. customAfter removing the catalyst
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over potassium carbonate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4da40cfde7f443c5bfd2239d4256aa10
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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