Ammonium Chloride → HCID 19592366, compound

HRID 613455Notes

Reaction equation

HRID 613455 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH3:15])=[CH:11][CH:10]=[CH:9][C:8]=2[N+:16]([O-])=O)(=[O:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH3:15])=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:16])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 19592329HCID 19592329, compound

Product 1

HCID 19592366HCID 19592366, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-acetyl-4-methoxy-8-nitroquinoline (230 mg), ammonium chloride (30 mg) and iron (313 mg) in ethanol (3 ml) and water (0.8 ml) was refluxed for 2 hours. Insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, and the solution was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to give 3-acetyl-8-amino-4-methoxyquinoline (175.7 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd4b068ae2234367a042b64b77918d43
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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