HCID 21584389, compound → HCID 21584347, compound

HRID 369987Notes

Reaction equation

HRID 369987 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-340d4818321d41ff96406c925988648c
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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