HCID 21432704, compound → HCID 21432715, compound

HRID 2399104Notes

Reaction equation

HRID 2399104 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[N:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[N:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

Participants

5

Reactant 2

HCID 21432704HCID 21432704, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21432715HCID 21432715, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 6-nitrocinnolin-3-yl carboxylate (150 mg.) was dissolved in ethanol (20 ml.), and 30% w/w palladium on charcoal catalyst (20 mg.) was added. The solution was shaken in an atmosphere of hydrogen at room temperature and atmospheric pressure until the theoretical uptake had taken place. The catalyst was filtered off and the ethanol solution was evaporated to dryness, yielding a yellow solid. This solid was purified by chromatography on a column of Kieselgel 60 (E. Merck, Darmstadt) using ethyl acetate as eluent. The appropriate fractions were combined and evaporated to dryness to give ethyl 6-aminocinnolin-3-yl carboxylate, m.p. 204°-206° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe ethanol solution was evaporated to dryness
  3. customyielding a yellow solid
  4. customThis solid was purified by chromatography on a column of Kieselgel 60 (E. Merck, Darmstadt)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-769fbf7d3ae34bda908492396eaf94f5
Source dataset
uspto-grants-1977_05
Patent number
US04027023

Reaction notes

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