Potassium Nitrate → HCID 178481981, compound

HRID 1031084Notes

Reaction equation

HRID 1031084 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[OH:6][C:7]1[C:16]([OH:17])=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]3[N:20]=[N:19][N:18]([CH3:21])[C:13]3=2)[N:8]=1>S(=O)(=O)(O)O>[OH:6][C:7]1[C:16]([OH:17])=[N:15][C:14]2[C:9](=[CH:10][C:11]([N+:1]([O-:4])=[O:2])=[C:12]3[N:20]=[N:19][N:18]([CH3:21])[C:13]3=2)[N:8]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 178481973HCID 178481973, compound

Product 1

HCID 178481981HCID 178481981, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Finely powdered potassium nitrate (0.71 g, 7 mmol) was added portionwise to a stirred solution of 7,8-dihydroxy-1-methyl-1H-1,2,3-triazolo[4,5-f]quinoxaline (1.52 g, 7 mmol) in 28 ml of conc. sulfuric acid at 0° C. After about 1 h the ice bath was removed and stirring was continued over night at room temperature. Then an additional amount of potassium nitrate (0.7 g) was added and the mixture was stirred for 4 h at room temperature. Now the solution was poured into 150 ml of ice/water and the precipitated yellow solid was isolated by filtration and washed with water. Recrystallization from water/ethanol (1:1) afforded 1.2 g (65%) of the pure nitro compound; m.p. >300° C.; IR (KBr): 3600-2500, 1720 cm-1 ; 1H-NMR (DMSO-d6): 4.62 (s,3H, CH3), 8.07 (s, 1H, ArH), 12.4 (broad s, 1H, OH, only one exchangeable proton could be seen).

Workup

  1. customAfter about 1 h the ice bath was removed
  2. waitwas continued over night at room temperature
  3. additionThen an additional amount of potassium nitrate (0.7 g) was added
  4. stirringthe mixture was stirred for 4 h at room temperature
  5. additionNow the solution was poured into 150 ml of ice/water
  6. customthe precipitated yellow solid was isolated by filtration
  7. washwashed with water
  8. customRecrystallization from water/ethanol (1:1)

Sources & evidence

ORD record
ord-c6896fe0076b4cff9687b464df8ffea7
Source dataset
uspto-grants-1992_04
Patent number
US05109001

Reaction notes

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