Methane → 5-Aminoacenaphthene

HRID 54463

Reaction equation

HRID 54463 reaction equation
[N+:1]([C:4]1[C:14]2[C:15]3[C:7]([CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.C>O1CCCC1.C(O)(=O)C.C(Cl)Cl.[Pd]>[NH2:1][C:4]1[C:14]2[C:15]3[C:7]([CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 297MethaneHCID 117695-Nitroacenaphthene

Product 1

HCID 625475-Aminoacenaphthene

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

40 gms (Aldrich lot #CY 02301 HX, containing 15% of the 3-nitro isomer) of 5-nitroacenaphthene was dissolved in a mixture of tetrahydrofuran (150 ml) and acetic acid (25 ml.). To this solution was added 1.0 of 10% Pd/C and the mixture hydrogenated (40 psi) at room temperature. After 2 hours, the mixture was filtered through a bed of celite and the filtrate concentrated in vacuo to give a mixture of a solid which darkened (to purple) considerably on exposure to air. This material was redissolved in methylene chloride and decolorized with activated charcoal and then the product recrystallized from a mixture of cyclohexane:ethyl acetate (3:1) to give 8.3 g of clean material--only the major 5-amino isomer being present by TLC. This material was used as is directly in the next step.

Workup

  1. customat room temperature
  2. filtrationthe mixture was filtered through a bed of celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give
  5. additiona mixture of a solid which
  6. customthe product recrystallized from a mixture of cyclohexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-5fefe3598c414c188fafb39f98450eee
Source dataset
uspto-grants-1997_04
Patent number
US05622968

Linked notes

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