N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine → 1,1-Dimethyl-2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethanol

HRID 547334Notes

Reaction equation

HRID 547334 reaction equation
[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O>[Pt].C(O)(C)C>[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15]

Participants

4

Reactant 1

HCID 22172695N-(2-hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

Product 1

HCID 221726871,1-Dimethyl-2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethanol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

N-(2-Hydroxy-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (44.12 g, 0.17 mol), 5% platinum on carbon (4.4 g) and isopropanol (890 mL) were combined in a Parr vessel and placed under hydrogen pressure (35 psi, 2.4×105 Pa) overnight. The reaction mixture was filtered through a layer of filtering agent. The layer of filtering agent was rinsed well with isopropanol. The filtrate was concentrated under reduced pressure to provide N4-(2-hydroxy-2-methylpropyl)[1,5]naphthyridin-3,4-diamine as a thick oil.

Workup

  1. custompressure (35 psi, 2.4×105 Pa) overnight
  2. filtrationThe reaction mixture was filtered through a layer
  3. filtrationof filtering agent
  4. filtrationThe layer of filtering agent
  5. washwas rinsed well with isopropanol
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0750b168792476d878705706eb0af04
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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