HCID 44248848, compound → HCID 44248849, compound

HRID 1443897Notes

Reaction equation

HRID 1443897 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11]3=[C:12]([C:14]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]=4[N:10]3[CH2:9][CH2:8][CH2:7]2)[CH:13]=1)([O-])=O>[Pd].C(O)C>[CH:13]1[C:12]2[C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[N:10]3[C:11]=2[C:6]([CH2:7][CH2:8][CH2:9]3)=[CH:5][C:4]=1[NH2:1]

Participants

4

Reactant 1

HCID 44248848HCID 44248848, compound

Product 1

HCID 44248849HCID 44248849, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-nitro-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline (0.30 g, 11 mmol) and 5% palladium on carbon (0.10 g) in ethanol (35 mL) was shaken on a Parr hydrogenator under an atmosphere of hydrogen (45 PSI) for 48 h. The reaction mixture was filtered through Celite® and the filter bed was washed with ethanol. The filtrate was concentrated to provide 0.27 g of 5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-amine.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe filter bed was washed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e1a82c757aed4b08903963cf6b694889
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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