N4-(3-isopropoxypropyl)-3-nitro[1,5]naphthyridin-4-amine → N4-(3-isopropoxypropyl)[1,5]naphthyridine-3,4-diamine

HRID 2057022Notes

Reaction equation

HRID 2057022 reaction equation
[CH:1]([O:4][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)([CH3:3])[CH3:2]>[Pt].C(OCC)(=O)C>[CH:1]([O:4][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])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 54329107N4-(3-isopropoxypropyl)-3-nitro[1,5]naphthyridin-4-amine

Product 1

HCID 54100366N4-(3-isopropoxypropyl)[1,5]naphthyridine-3,4-diamineYield 95.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N4-(3-Isopropoxypropyl)-3-nitro[1,5]naphthyridin-4-amine (4.2 g, 14.5 mmol), platinum on carbon (1.1 g of 5%), and ethyl acetate (100 mL) were placed in a hydrogenation flask. The mixture was shaken under a hydrogen pressure of 50 psi (3.5 Kg/cm2) for 2.5 hours. The reaction mixture was filtered and the catalyst was washed with ethyl acetate. The filtrate was dried over magnesium sulfate, filtered and then concentrated under vacuum to provide 3.6 g of N4-(3-isopropoxypropyl)[1,5]naphthyridine-3,4-diamine as a bright yellow oil. 1H NMR (300 MHz, CDCl3): δ 8.70 (dd, J=4.1, 1.6 Hz, 1H), 8.39 (s, 1H), 8.17 (dd, J=8.4, 1.6 Hz, 1H), 7.37 (dd, J=8.4, 4.1 Hz, 1H), 5.99 (broad s, 1H), 3.98 (broad s, 2H), 3.63-3.55 (m, 5H), 1.87 (pentet, J=6.2 Hz, 2H), 1.17 (d, J=6.1 Hz, 6H); MS (EI): m/e 260.1630 (260.1637 calc'd for C14H20N4O).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe catalyst was washed with ethyl acetate
  3. dry with materialThe filtrate was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3844eb72a633423ea7949c9511a3aae5
Source dataset
uspto-grants-2008_02
Patent number
US07335773B2

Reaction notes

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