HCID 21584389, compound → HCID 21584347, compound

HRID 583288Notes

Reaction equation

HRID 583288 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][CH:10]3[CH2:17][CH2:16][CH2:15][N:11]3[CH2:12][C:13]=2[CH:14]=1)([O-])=O>CO.[Pd]>[ClH:1].[CH2:17]1[CH:10]2[N:11]([CH2:12][C:13]3[CH:14]=[C:5]([NH2:2])[CH:6]=[CH:7][C:8]=3[CH2:9]2)[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 21584389HCID 21584389, compound

Product 1

HCID 21584347HCID 21584347, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 7-nitro-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline hydrochloride (2.14 g, 8.40 mmol) in methanol (150 ml) was added 10% Pd/C (0.2 g) and the reaction mixture was hydrogenated at 50 psi for 2 h. The solution was filtered and the catalyst was washed with water to dissolve some precipitated product. The filtrate was concentrated and absolute ethanol was used to help evaporate the excess water. The resulting solid was dissolved in hot ethanol (50 ml) and ether was added to precipitate the product. This solid was collected to give the title compound (1.90 g, 100%) as an amorphous, off-white solid, MS 189 (M+H)+ ; NMR (DMSO-NaOD) 6.82 (d, 1H), 6.44 (d, 1H), 6.35 (s, 1H), 4.03 (d, 1H), 3.19 (broad s, 1H), 2.84 (d, 1H), 2.5-3.0 (m, 3H), 2.11 (broad s 1H), 2.7-2.9 (m, 2H), 1.52 (m, 1H).

Workup

  1. filtrationThe solution was filtered
  2. washthe catalyst was washed with water
  3. dissolutionto dissolve some precipitated product
  4. concentrationThe filtrate was concentrated
  5. customto help evaporate the excess water
  6. dissolutionThe resulting solid was dissolved in hot ethanol (50 ml)
  7. additionether was added
  8. customto precipitate the product
  9. customThis solid was collected

Sources & evidence

ORD record
ord-4e4165890c924f1ebb8bf70d47dcc076
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

Loading…