Furan → HCID 178470437, compound

HRID 442339Notes

Reaction equation

HRID 442339 reaction equation
Cl.N[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[N:8][C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2[OH:18].N([O-])=O.[Na+].S([O-])([O-])(=O)=O.[Mg+2].[O:29]1[CH:33]=[CH:32][CH:31]=[CH:30]1.O.O.O.C([O-])(=O)C.[Na+]>O.Cl>[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[N:8][C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2[OH:18]

Participants

8

Reactant 5

HCID 8029FuranHCID 24083Sulfuric acid magnesium salt (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 23668193Sodium NitriteHCID 178470448HCID 178470448, compound

Product 1

HCID 178470437HCID 178470437, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate hydrochloride (1.164 g.) in water (10 ml.) and concentrated hydrochloric acid (1.0 ml.) was stirred at 0° C. in an ice-salt bath, and a solution of sodium nitrite (0.5 g.) in water (3 ml.) was added during 5 minutes, maintaining the temperature at 0°-5° C. The mixture was stirred for 10 minutes at 0° C., and then magnesium sulphate (0.020 g.), furan (20 ml.) and sodium acetate trihydrate (4 g.) were added. The reaction mixture was stirred vigorously, allowed to warm to room temperature and stirred vigorously for 48 hours. The mixture was extracted with ethyl acetate (4 × 100 ml.). The combined extracts were washed with water, dried (MgSO4), filtered, and evaporated under reduced pressure. The oily brown residue was dissolved in ethyl acetate and applied to a silica column (30 g., Kieselgel 60). Elution with ethyl acetate yielded ethyl 6-furyl-4-hydroxycinnolin-3-yl carboxylate, m.p. 198°-200° C.

Workup

  1. temperaturemaintaining the temperature at 0°-5° C
  2. stirringThe mixture was stirred for 10 minutes at 0° C.
  3. stirringThe reaction mixture was stirred vigorously
  4. temperatureto warm to room temperature
  5. stirringstirred vigorously for 48 hours
  6. extractionThe mixture was extracted with ethyl acetate (4 × 100 ml.)
  7. washThe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. dissolutionThe oily brown residue was dissolved in ethyl acetate
  12. washElution with ethyl acetate

Sources & evidence

ORD record
ord-d81b6d32a4e1432e856c9904d7611421
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

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