HCID 11458385, compound → HCID 21701862, compound

HRID 1027910Notes

Reaction equation

HRID 1027910 reaction equation
[N+:1]([C:4]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14](=O)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)(=O)C.[Pd]>[C:4]1([NH2:1])[CH:5]=[CH:6][CH:7]=[C:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]=12

Participants

5

Reactant 2

HCID 11458385HCID 11458385, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21701862HCID 21701862, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulene-5-one (CAS #251554-42-4, 2.5 g, 12 mmol), palladium (413 mg, 10% on carbon, 0.4 mmol) in acetic acid (25 ml) under the hydrogen atmosphere (60 PSI) was heated at 60° C. and stirred at for 16 hours. 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 1.50-1.69 (m, 4H), 1.75-1.86 (m, 2H), 2.71-2.86 (m, 4H), 5.46 (s, 2H), 7.03-7.12 (m, 3H). MS (M+H)+ m/z 162.

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-25d5bc22a7814628bf4159cc0404bf9a
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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