Ammonium formate → 3-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

HRID 274053Notes

Reaction equation

HRID 274053 reaction equation
C([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][CH2:15][CH:9]([NH2:8])[CH2:10][C:11]=2[CH:19]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18007303HCID 18007303, compound

Product 1

HCID 180073203-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amineYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (68.7 g), ammonium formate (68.15 g), and 10% palladium on carbon (50% wet; 6.8 g) in ethanol (1.2 l) was refluxed for 1 hour. After cooling, the catalyst was filtered off and the solvent was removed in vacuo. To the residue, water and 28% ammonium hydroxide were added and the whole was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (35.8 g) as an oil.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe catalyst was filtered off
  4. customthe solvent was removed in vacuo
  5. additionTo the residue, water and 28% ammonium hydroxide were added
  6. extractionthe whole was extracted with ethyl acetate
  7. washThe extract was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-110dff997583407f96821aaa06daacad
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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