HCID 22124678, compound → HCID 22124615, compound

HRID 1857965Notes

Reaction equation

HRID 1857965 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]1=[O:20])[CH3:2].[H][H]>[Ni].C(O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:20])[CH3:2]

Participants

5

Reactant 2

HCID 22124678HCID 22124678, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22124615HCID 22124615, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-ethyl-7-phenylamino-1H-[1,6]naphthyridin-2-one from Example W (75 mg, 0.29 mmol), 0.6 g of Raney nickel, and 50 mL of ethanol was stirred under 50 psi of hydrogen at room temperature for 23 hours. The suspension was filtered and the filtrate was concentrated to a solid residue that was purified by preparative thin layer chromatography to give 1-ethyl-7-phenylamino-3,4-dihydro-1H-[1,6]naphthyridin-2-one (10 mg, 13% yield): mp 137-138° C.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated to a solid residue that
  3. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1528251227394e3ea3a9b456b3d5cb6b
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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