HCID 86759575, compound → HCID 69918840, compound

HRID 2307440Notes

Reaction equation

HRID 2307440 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[N:20]O)[CH3:19])[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][CH:14]=[C:15]([CH:18]([NH2:20])[CH3:19])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86759575HCID 86759575, compound

Product 1

HCID 69918840HCID 69918840, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 444642Hydroxy-nickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-(1-hydroxyiminoethyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (1.0 g, 3.44 mmol) in MeOH (50 ml) was hydrogenated for 1 h under a pressure of 44 psi, in presence of 50% RaNi/H2O (2 mL). Additional catalyst was added (1 mL) and the hydrogenation proceeded for 3 hours. The catalyst was filtered off and filtrate evaporated. The crude product was chromatographed (SiO2, 15% of 2.0M NH3/MeOH in CH3CN) to provide 0.72 g (76%) of the title compound as a white solid. m.p: 61-64° C.

Workup

  1. additionAdditional catalyst was added (1 mL)
  2. filtrationThe catalyst was filtered off
  3. customfiltrate evaporated
  4. customThe crude product was chromatographed (SiO2, 15% of 2.0M NH3/MeOH in CH3CN)

Sources & evidence

ORD record
ord-94cf20382d3648e6a6a0373fcc726a6c
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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