N5-(2-methylpropyl)4-nitrotetrazolo[1,5-a][1,7]naphthyridin-5-amine → N5-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-4,5-diamine

HRID 1168356Notes

Reaction equation

HRID 1168356 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][N: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.S.[Na]>C(O)(=O)C.O>[CH3:1][CH:2]([CH3:21])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][N: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 12015802N5-(2-methylpropyl)4-nitrotetrazolo[1,5-a][1,7]naphthyridin-5-amineHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 12015803N5-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-4,5-diamineYield 90.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

N5-(2-Methylpropyl)-4-nitrotetrazolo[1,5-a][1,7]naphthyridin-5-amine (1.5 g, 5.22 mmol) was suspended in acetic acid (75 mL). An excess of sodium hydrogen sulfide was dissolved in a minimum of water and added to the suspension. The reaction mixture turned red and all of the material went into solution. The reaction mixture was extracted twice with dichloromethane (150 mL). The extracts were combined, washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum to provide 1.22 g of N5-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-4,5-diamine as a light yellow solid, m.p. 203-204.5° C. Analysis: Calculated for: C12H15N7: %C, 56.02; %H, 5.88; %N, 38.11; Found: %C, 55.68; %H, 5.81; %N, 37.74.

Workup

  1. additionadded to the suspension
  2. extractionThe reaction mixture was extracted twice with dichloromethane (150 mL)
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f455f0bd59c64ca8845cc3ff8e311886
Source dataset
uspto-grants-2003_09
Patent number
US06624172B2

Reaction notes

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