Sulfuric acid magnesium salt (1:1) → N4-Isobutyl-1,5-naphthyridine-3,4-diamine

HRID 47472Notes

Reaction equation

HRID 47472 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[CH3:7][CH:8]([CH3:24])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][N:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-])=O.[H][H]>[Pt].C(OCC)(=O)C>[CH3:7][CH:8]([CH3:24])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][N:19]=2)[N:14]=[CH:13][C:12]=1[NH2:21]

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 54184816N-(2-Methylpropyl)-3-nitro-1,5-naphthyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 53699038N4-Isobutyl-1,5-naphthyridine-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Magnesium sulfate (3 g) and a catalytic amount of 5% platinum on carbon were added to a solution of N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (3.0 g, 12.2 mmol) in ethyl acetate (150 mL). The reaction mixture was reduced on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen for four hours. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under vacuum to provide N4-(2-methylpropyl)[1,5]naphthyridin-3,4-diamine as a crude solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-90726a41ca0e45fa91e2ac127f08208e
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Reaction notes

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