3-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one → 3-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

HRID 1027908Notes

Reaction equation

HRID 1027908 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 3444873-Nitro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 2668073-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulene-5-one (CAS #7507-93-9, 2 g, 9.75 mmol), palladium (413 mg, 10% on carbon, 0.4 mmol) in methanol (25 ml) under the hydrogen atmosphere (60 PSI) was stirred at room temperature for 16 hrs. The mixture was filtered through a layer of diatomaceous earth, washed with methanol and concentrated under reduced pressure to provide the title compound. 1H NMR (CDCl3) δ 1.77-1.84 (m, 4H), 2.67-2.73 (m, 2H), 2.82 (t, J=6.10 Hz, 2H), 6.75 (dd, J=8.14, 2.71 Hz, 1H), 6.99 (d, J=8.48 Hz, 1H), 7.05 (d, J=2.71 Hz, 1H). MS (M+H)+ m/z 175.

Workup

  1. filtrationThe mixture was filtered through a layer of diatomaceous earth
  2. washwashed with methanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a6c1792b68546b78d92d9d8112fb0ff
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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