Acetic Acid → HCID 67263886, compound

HRID 1687071Notes

Reaction equation

HRID 1687071 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]2[CH:11]3CC[N:7]([CH2:8][CH2:9][CH2:10]3)[C:6]=2[CH:5]=1)([O-])=O.[C:17](O)(=O)[CH3:18]>CO.[Pd]>[CH:12]12[CH2:11][CH2:10][CH:9]([CH2:8][NH:7][CH2:6]1)[C:18]1[C:13]2=[CH:14][C:4]([NH2:1])=[CH:5][CH:17]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67264332HCID 67264332, compound

Product 1

HCID 67263886HCID 67263886, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Nitro-1-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene (250 mg, 1.15 mmol) was placed in methanol (10 mL) and acetic acid (0.2 mL). 10% Palladium on carbon (6.8 mg) was then added. The reaction was hydrogenated at 50 psi for 3 hours. The mixture was then filtered through celite and concentrated under reduced pressure. The residue was taken up in toluene (20 mL) and concentrated under reduced pressure to obtain 10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamine as a light brown oil (193 mg, 89%). LCMS (m/e) 189 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.89 (d, 1H, J=7.8 Hz), 6.53 (dd, 1H, J=2.4 and 7.8 Hz), 6.48 (d, 1H, J=2.3 Hz), 3.20-2.80 (m, 8H), 2.02 (d, 2H, J=8.7 Hz), 1.82 (d, 2H, J=10.7 Hz).

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b3cce4bd7d34361bfa62fae0e9f4850
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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