2-Methoxy-10-(2-nitroethyl)-6,7,8,9-tetrahydropyrido[2,3-b]indolizine → 2-(2-Methoxy-6,7,8,9-tetrahydropyrido[2,3-b]indolizin-10-yl)ethylamine

HRID 1767556Notes

Reaction equation

HRID 1767556 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH2:15][CH2:16][N+:17]([O-])=O)[C:7]=2[N:20]=1>[Ni].CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH2:15][CH2:16][NH2:17])[C:7]=2[N:20]=1

Participants

4

Reactant 1

HCID 120351202-Methoxy-10-(2-nitroethyl)-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

Product 1

HCID 187582342-(2-Methoxy-6,7,8,9-tetrahydropyrido[2,3-b]indolizin-10-yl)ethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Under a hydrogen pressure of 55 psi, 420 mg (1.53 mmol) of the compound obtained in Step E and 170 mg of Raney nickel are stirred in 20 ml of methanol at 60° C. for 15 hours. After returning to room temperature, the reaction mixture is filtered using a Büchner funnel and then evaporated to yield the title product in the form of a brown oil.

Workup

  1. customAfter returning to room temperature
  2. filtrationthe reaction mixture is filtered
  3. customevaporated

Sources & evidence

ORD record
ord-e3b7dacc50574d5ab87f9b0812becabf
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

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