N-(2-methylpropyl)4-nitrotetrazolo[1,5-a][1,8]naphthyridine-5-amine → N5-(2-methylpropyl)tetrazolo(1,5-a][1,8]naphthyridin-4,5-diamine

HRID 1168348Notes

Reaction equation

HRID 1168348 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]2[N:15]=[N:16][N:17]=[C:7]2[C:6]=1[N+:18]([O-])=O.[H][H]>[Pt].C(O)C>[CH3:1][CH:2]([CH3:21])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]2[N:15]=[N:16][N:17]=[C:7]2[C:6]=1[NH2:18]

Participants

5

Reactant 2

HCID 53835129N-(2-methylpropyl)4-nitrotetrazolo[1,5-a][1,8]naphthyridine-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 53865550N5-(2-methylpropyl)tetrazolo(1,5-a][1,8]naphthyridin-4,5-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A catalytic amount of 5% platinum on carbon was added to a suspension of N5-(2-methylpropyl)-4-nitrotetrazolo[1,5-a][1,8]naphthyridine-5-amine (5 g, 17.4 mmoles) in ethanol (300 mL). The reaction mixture was reduced on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen for 2 hours. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum to provide N5-(2-methylpropyl)tetrazolo[1,5-a][1,8]naphthyridin-4,5-diamine as an oil.

Workup

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

Sources & evidence

ORD record
ord-909e10f44c494ceda674e7d6ac1be592
Source dataset
uspto-grants-2003_09
Patent number
US06624172B2

Reaction notes

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