N-(2-Methylpropyl)-3-nitro-1,5-naphthyridin-4-amine → N4-Isobutyl-1,5-naphthyridine-3,4-diamine

HRID 352484Notes

Reaction equation

HRID 352484 reaction equation
[CH3:1][CH:2]([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.[H][H]>[Pt].C(OCC)(=O)C>[CH3:1][CH:2]([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

5

Reactant 2

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

A catalytic amount of 5% platinum on carbon was added to a solution of N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (1.0 g, 4.1 mmol) in ethyl acetate (50 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-50a899cab6ce44788019464749127f16
Source dataset
uspto-grants-2004_06
Patent number
US06747040B2

Reaction notes

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