HCID 57455387, compound → HCID 86612242, compound

HRID 1623093Notes

Reaction equation

HRID 1623093 reaction equation
[CH2:1]([O:3][CH:4]([O:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-])=O)[CH3:2]>[Pt].C(OCC)(=O)C>[CH2:23]([O:22][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=[CH:11][C:10]=1[NH2:19])[CH3:24]

Participants

4

Reactant 1

HCID 57455387HCID 57455387, compound

Product 1

HCID 86612242HCID 86612242, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Catalyst (0.78 g of 5% platinum on carbon) was added to a suspension of (4,4-diethoxybutyl)(3-nitro[1,5]naphthyridin-4-yl)amine (7.8 g, 23.3 mmol) in ethyl acetate (100 mL). The mixture was placed under hydrogen pressure ((30 psi (2.1×105 Pa)) for 2 hours. The reaction mixture was filtered through a layer of CELITE filter aid and the filter cake was rinsed with ethyl acetate (40 mL). The filtrate was concentrated under reduced pressure to provide N4-(4,4-diethoxybutyl)[1,5]naphthyridine-3,4-diamine as a thick yellow oil which was carried on to the next without further purification.

Workup

  1. customfor 2 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was rinsed with ethyl acetate (40 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c294f99d7c5441b997c163893ceb5a72
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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