HCID 178526410, compound → HCID 178507219, compound

HRID 1165810Notes

Reaction equation

HRID 1165810 reaction equation
[OH:1][C:2]1[C:3]([OH:19])=[N:4][C:5]2[CH:6]=[C:7]([N+:16]([O-])=O)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1>Cl>[NH2:16][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]2[N:11]=[C:2]([OH:1])[C:3]([OH:19])=[N:4][C:5]=2[CH:6]=1

Participants

3

Reactant 1

HCID 178526410HCID 178526410, compound

Product 1

HCID 178507219HCID 178507219, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of stannous chloride dihydrate (3.7 g, 16 mmol) in 10 ml of conc. hydrochloric acid was added dropwise to a stirred suspension of 2,3-dihydroxy-6-nitrobenzo(f)quinoxaline (1.3 g, 5 mmol) in 8 ml of conc. hydrochloric acid. Then the mixture was stirred at 60-70° C. on an oil bath for 2 h. After cooling on ice, the precipitate was collected, dissolved in boiling water (1 1), filtered while hot, and neutralized to pH 6 with solid sodium hydrogen carbonate. The yellow product was isolated and recrystallized from DMF/water, washed with water, ethanol and ether and finally dried at 110 ° C. to give 0.90 g (63%) of pure title compound, m.p. >300° C., IR (KBr): 1690, ? 1640 and 1605 cm-1,1H-NMR (DMSO-d6): 5.8 (broad s, 2H,NH2), 6.63(s,1H, H-5), 7.2-8.7 (m, 4H, ArH), 11.8 (broad s, 2H, 20H).

Workup

  1. temperatureAfter cooling on ice
  2. customthe precipitate was collected
  3. dissolutiondissolved
  4. filtrationfiltered while hot, and neutralized to pH 6 with solid sodium hydrogen carbonate
  5. customThe yellow product was isolated
  6. customrecrystallized from DMF/water
  7. washwashed with water, ethanol and ether
  8. customfinally dried at 110 ° C.

Sources & evidence

ORD record
ord-dcc1a5efa86d4d09b08ec14f86ec1748
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

Loading…