HCID 86589153, compound → tert-butyl 6-(1-aminoethyl)-3,4-dihydro-2H-quinoline-1-carboxylate

HRID 2307442Notes

Reaction equation

HRID 2307442 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=[N:20]O)[CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni].O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]([NH2:20])[CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86589153HCID 86589153, compound

Product 1

HCID 67550893tert-butyl 6-(1-aminoethyl)-3,4-dihydro-2H-quinoline-1-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 444642Hydroxy-nickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-(1-hydroxyimino-ethyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (1.0 g, 3.44 mmol), dissolved in MeOH (50 mL), was hydrogenated under a pressure of 40 psi in the presence of 50% RaNi/H2O (3 mL) for 5 hours. The catalyst was filtered off and the solvent evaporated. The crude amine was purified by chromatography (SiO2, 15% of 2.0M NH3/MeOH in CH3CN) to give 0.57 g (60%) of the title compound as a white solid. m.p: 73-75° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customThe crude amine was purified by chromatography (SiO2, 15% of 2.0M NH3/MeOH in CH3CN)

Sources & evidence

ORD record
ord-d861de6357594bf988fc83876a58ee5c
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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