Acetic Anhydride → 1-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene

HRID 2257858Notes

Reaction equation

HRID 2257858 reaction equation
[N+:1]([C:4]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[C:15](OC(=O)C)(=[O:17])[CH3:16]>[Ni].C(O)(=O)C>[C:15]([NH:1][C:4]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 224495161-nitro-6,7,8,9-tetrahydro-5H-benzocycloheptene

Product 1

HCID 102623081-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

8.7 gm of 1-nitro-6,7,8,9-tetrahydro-5H-benzocycloheptene [J. Am. Chem. Soc., 5820 (9169)] was dissolved into a mixed solvent of 150 ml of acetic anhydride and 50 ml of acetic acid. The mixture was catalytically hydrogenated with the addition of 10 ml of raney nickel. After removing the catalyst by filtration, the reaction mixture was concentrated, the residue was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. The product was concentrated to produce 6.17.gm of the title compound.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe reaction mixture was concentrated
  4. washthe residue was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe product was concentrated

Sources & evidence

ORD record
ord-249c5781544b4edb87ff2e7cc51a071b
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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