HCID 11107934, compound → HCID 11119004, compound

HRID 1858151Notes

Reaction equation

HRID 1858151 reaction equation
[N:1]([O-])=O.[Na+].[NH:5]([C:7]1[C:16]2[N:17]=[CH:18][N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1)[NH2:6]>O.C(O)(=O)C>[CH3:22][CH:21]([CH3:23])[CH2:20][N:19]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]3[N:1]=[N:6][N:5]=[C:7]3[C:16]=2[N:17]=[CH:18]1

Participants

5

Reactant 2

HCID 11107934HCID 11107934, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11119004HCID 11119004, compoundYield 375.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (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-1d926f8a1c3146779fdfc988741e9a95
Source dataset
uspto-grants-2000_11
Patent number
US06150523

Reaction notes

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