2-Nitro-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one → 2-Amino-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one

HRID 1687002Notes

Reaction equation

HRID 1687002 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9][C:8]=2[CH:15]=1)([O-])=O>C1COCC1.Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9][C:8]=2[CH:15]=1

Participants

4

Reactant 1

HCID 457903192-Nitro-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one

Product 1

HCID 450982242-Amino-8,9-dihydro-5H-benzo[7]annulen-7(6H)-oneYield 91.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-nitro-5,6,8,9-tetrahydrobenzocyclohepten-7-one (0.5 g, 0.002 mol) in THF (125 mL) was added stannous chloride in conc. HCl (4 mL) over a 5 minute period. During this time the reaction mixture got very hot but not to reflux. The reaction mixture was stirred at room temperature for 2 h. The mixture continued to stir at room temperature overnight. HPLC showed no starting material remaining. The reaction mixture was concentrated in vacuo to remove all of the volatiles and the residue dissolved in water and made basic with 6N sodium hydroxide. The suspension was filtered through celite and washed well with chloroform. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give 2-amino-5,6,8,9-tetrahydro-benzocyclohepten-7-one (0.32 g, 70% yield). 1HNMR (400 MHz, DMSO-d6) δ 6.87 (d, 1H, J=8 Hz), 6.46 (s, 1H), 6.38 (d, 1H, J=8 Hz), 4.83 (s, 2H), 2.68 (m, 4H), 2.44 (m, 4H).

Workup

  1. temperaturenot to reflux
  2. stirringto stir at room temperature overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove all of the volatiles
  5. dissolutionthe residue dissolved in water
  6. filtrationThe suspension was filtered through celite
  7. washwashed well with chloroform
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95143cbdf8c64582be0cfefcd86c3be2
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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