HCID 178481981, compound → HCID 178481980, compound

HRID 1089716Notes

Reaction equation

HRID 1089716 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([N+:17]([O-])=O)=[C:7]3[N:15]=[N:14][N:13]([CH3:16])[C:8]3=2)[N:3]=1>Cl>[NH2:17][C:6]1[CH:5]=[C:4]2[C:9]([N:10]=[C:11]([OH:12])[C:2]([OH:1])=[N:3]2)=[C:8]2[N:13]([CH3:16])[N:14]=[N:15][C:7]=12

Participants

3

Reactant 1

HCID 178481981HCID 178481981, compound

Product 1

HCID 178481980HCID 178481980, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of stannous chloride dihydrate (2.26 g, 10 mmol) in 10 ml of conc. hydrochloric acid was added dropwise to a suspension of 7,8-dihydroxy-1-methyl-4-nitro-lH-1,2,3-triazolo[4,5-f]quinoxaline (0.79 g, 3 mmol) in 5 ml of conc. hydrochloric acid with stirring on an oil bath at 60°-70° C. Stirring was continued at this temperature for 90 min. Then the mixture was cooled on an ice bath, and filtered. The precipitate was washed with 1 ml of conc. hydrochIoric acid, suspended in 150 ml of hot water, and adjusted to pH 6-7 with solid sodium hydrogen carbonate. After reflux for 1 h the mixture was cooled on ice and the crude product was isolated by filtration, dissolved in 4? ml of hot 2N sodium hydroxide and reprecipitated with 4M acetic acid giving 0.16 g (23%) of the pure amino compound; m.p. >300° C.; IR (KBr): 3435, 3350, 3240, 3100-2400, 1690, 1640 cm-1.

Workup

  1. stirringStirring
  2. temperatureThen the mixture was cooled on an ice bath
  3. filtrationfiltered
  4. washThe precipitate was washed with 1 ml of conc. hydrochIoric acid
  5. temperatureAfter reflux for 1 h the mixture
  6. temperaturewas cooled on ice

Sources & evidence

ORD record
ord-32a732f9c15046c282b4731b54556dbf
Source dataset
uspto-grants-1992_01
Patent number
US05079250

Reaction notes

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