HCID 19592399, compound → HCID 19592541, compound

HRID 613461Notes

Reaction equation

HRID 613461 reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([N+:15]([O-])=O)[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3]>C(O)(=O)C.C(O)C.[Fe]>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][CH:6]=[C:5]2[O:4][CH2:1][CH:2]=[CH2:3]

Participants

5

Reactant 1

HCID 19592399HCID 19592399, compound

Product 1

HCID 19592541HCID 19592541, compoundYield 90.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-allyloxy-8-nitroquinoline (110 mg) and iron (268 mg) in acetic acid (0.4 ml) and ethanol (1.6 ml) was refluxed for 1 hour. Insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane, and the solution was washed with saturated sodium bicarbonate solution and water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate-n-hexane) to give 8-amino-4-allyloxyquinoline (87 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe solution was washed with saturated sodium bicarbonate solution and water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-6a73a280fc734e4789b9064fbbb645f3
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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