HCID 178526774, compound → HCID 178508000, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[N:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>O.C(N(CC)CC)C.[Pt]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[N:11][CH:10]=[CH:9][CH:8]=2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
3-Nitro[1,5]naphthyridin-4-ol (40 g, 0.2 mol) was dissolved in water (80 mL) and triethylamine (60 mL), and the solution was added to a Parr vessel. Platinum on carbon (1.0 g of 5%) was added, and the mixture was shaken under hydrogen pressure (40 psi, 2.8×105 Pa) overnight. The vessel was pressurized again, and the mixture was shaken under hydrogen pressure for four hours. The vessel was purged with nitrogen, and the reaction mixture was filtered through a layer of CELITE filter agent. The filter cake was washed with water and methanol, and the filtrate was concentrated under reduced pressure to a volume of 150 mL. A precipitate formed and was isolated by filtration to provide 24.6 g of 3-amino[1,5]naphthyridin-4-ol as a yellow solid. The filter cake was washed again with water (500 mL at 80° C.), and the filtrate was concentrated to a volume of 100 mL. A precipitate formed and was isolated by filtration to provide an additional 10.7 g of 3-amino[1,5]naphthyridin-4-ol as a yellow solid.
Workup
- stirringthe mixture was shaken under hydrogen pressure for four hours
- customThe vessel was purged with nitrogen
- filtrationthe reaction mixture was filtered through a layer of CELITE filter agent
- washThe filter cake was washed with water and methanol
- concentrationthe filtrate was concentrated under reduced pressure to a volume of 150 mL
- customA precipitate formed
- customwas isolated by filtration
Sources & evidence
- ORD record
- ord-d525fb4659474f6891ce1fa5c9f1da40
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07579359B2
Reaction notes
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