Sodium Nitrate → HCID 11119004, compound

HRID 1168566Notes

Reaction equation

HRID 1168566 reaction equation
[N+:1]([O-])([O-])=O.[Na+].[NH:6]([C:8]1[C:17]2[N:18]=[CH:19][N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)[NH2:7]>O.C(O)(=O)C>[CH3:23][CH:22]([CH3:24])[CH2:21][N:20]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]3[N:1]=[N:7][N:6]=[C:8]3[C:17]=2[N:18]=[CH:19]1

Participants

5

Reactant 2

HCID 24268Sodium NitrateHCID 11107934HCID 11107934, compound

Product 1

HCID 11119004HCID 11119004, compoundYield 375.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrate (2.0 g, 3 mmole) in water (5 mL) was added to a solution of 4-hydrazino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (4.0 g, 15.7 mmole, Example 7) in a mixture of acetic acid (5 mL) and water (50 mL). The reaction mixture was stirred at ambient temperature for 15 minutes. A precipitate was isolated by filtration, washed with water then air dried to provide 4.1 g of crude product. This material was recrystallized from dichloromethane/ethanol to provide 3.0 g of 6-(2-methylpropyl)-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline as a cream colored crystalline solid, m.p. 208-212° C. Analysis: Calculated for C14H14N6: %C, 63.14; %H, 5.30; %N, 31.56; Found: %C, 62.60; %H, 5.2; %N, 31.5.

Workup

  1. customA precipitate was isolated by filtration
  2. washwashed with water
  3. customair dried
  4. customto provide 4.1 g of crude product
  5. customThis material was recrystallized from dichloromethane/ethanol

Sources & evidence

ORD record
ord-4be2f6ad3acb4a8cada68c8f02a6131a
Source dataset
uspto-grants-2003_09
Patent number
US06624305B2

Reaction notes

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