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

HRID 1168355Notes

Reaction equation

HRID 1168355 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][CH:6]([CH3:22])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][N:15]=[CH:16][CH:17]=2)[N:12]2[N:19]=[N:20][N:21]=[C:11]2[CH:10]=1>C(O)(=O)C>[CH3:5][CH:6]([CH3:22])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][N:15]=[CH:16][CH:17]=2)[N:12]2[N:19]=[N:20][N:21]=[C:11]2[C:10]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 12015801HCID 12015801, compound

Product 1

HCID 12015802N5-(2-methylpropyl)4-nitrotetrazolo[1,5-a][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Nitric acid (2 equivalents of 16M) was added to a solution of N5-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-5-amine (2.0 g, 8.26 mmol) in acetic acid. The reaction mixture was heated on a steam bath for about an hour then concentrated under vacuum. The residue was poured into ice water and the resulting mixture was neutralized with sodium bicarbonate. The resulting precipitate was extracted with dichloromethane. The dichloromethane extracts were combined, washed with water, and dried over magnesium sulfate. Thin layer chromatography indicated a mixture so the material was filtered through a layer of silica gel eluting with 5% ethyl acetate in dichloromethane. The reaction was rerun on 4 g of starting material but using only one equivalent of nitric acid. The resulting material was also a mixture. The material from both reactions was combined then purified by flash chromatography eluting with mixtures of hexanes/ethyl acetate. The fractions containing the slower moving material were combined to provide about 0.3 g of N5-(2-methylpropyl)-4-nitrotetrazolo[1,5-a][1,7]naphthyridin-5-amine as a yellow solid, m.p. 173-174° C. Analysis: Calculated for C12H13N7O2: %C, 50.17; %H, 4.56; %N, 34.13; Found: %C, 49.85; %H, 4.53; %N, 34.26.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for about an hour
  2. concentrationthen concentrated under vacuum
  3. additionThe residue was poured into ice water
  4. extractionThe resulting precipitate was extracted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationwas filtered through a layer of silica gel eluting with 5% ethyl acetate in dichloromethane
  8. customThe material from both reactions was combined then purified by flash chromatography
  9. washeluting with mixtures of hexanes/ethyl acetate
  10. additionThe fractions containing the

Sources & evidence

ORD record
ord-60b5ecd8be1e49b8946217984b1434dd
Source dataset
uspto-grants-2003_09
Patent number
US06624172B2

Reaction notes

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