Ethanol → 2-Chloroquinolin-8-amine

HRID 2359393Notes

Reaction equation

HRID 2359393 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH4+].[Cl-].CCO>[Fe].O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 3194532-Chloro-8-nitroquinoline

Product 1

HCID 3465192-Chloroquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-chloro-8-nitroquinoline (1.02 grams), iron powder (2.05 grams) and NH4Cl (2.6 grams) in 5:1 EtOH:Water (50 mL) was refluxed for 9 hours. After the reaction was complete, the solution was cooled to 60° C. and filtered through celite. The cake was washed with isopropyl alcohol followed by ethyl acetate. The filtrate was concentrated to dryness, dissolved in ethyl acetate and washed with water, dilute aqueous NaHCO3, brine and dried (Na2SO4) and concentrated to an oil. The desired product crystallized with the addition of pentane, brown solid (0.818 grams).

Workup

  1. filtrationfiltered through celite
  2. washThe cake was washed with isopropyl alcohol
  3. concentrationThe filtrate was concentrated to dryness
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water, dilute aqueous NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to an oil
  8. customThe desired product crystallized with the addition of pentane, brown solid (0.818 grams)

Sources & evidence

ORD record
ord-c1354952c8a242a38440c9e1743a41a3
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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