Ammonium Chloride → HCID 57444323, compound

HRID 15834Notes

Reaction equation

HRID 15834 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)[CH2:15][CH2:14]2)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[Cl-].[NH4+]>CO.O.[Fe]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][C:21]3[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=3)[NH2:27])[CH2:17][CH2:18]2)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

6

Reactant 2

HCID 25517Ammonium Chloride2×HCID 574443228-Fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

Product 1

HCID 57444323HCID 57444323, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 8-fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline (0.126 g; 1 eq) in methanol (4 mL) was added dropwise to a suspension of iron powder (0.125 g; 7 eq) and ammonium chloride (0.119 g; 7 eq) in water (4 mL). The reactants were heated at reflux for 8 hours, with additional amounts of iron powder (total 0.125 g; 7 eq) and ammonium chloride (0.119 g; 7 eq) added in 3 portions during the reaction. The reaction mixture was cooled to room temperature and filtered using a Millipore filter. The filtrate was concentrated under reduced pressure, diluted with water (5 mL) and a saturated aqueous solution of sodium hydrogen carbonate (2 mL) and extracted into ethyl acetate (3×5 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to give the title compound in 77% yield (0.090 g).

Workup

  1. temperatureThe reactants were heated
  2. additionadded in 3 portions during the reaction
  3. filtrationfiltered
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additiondiluted with water (5 mL)
  7. extractiona saturated aqueous solution of sodium hydrogen carbonate (2 mL) and extracted into ethyl acetate (3×5 mL)
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61a39b96fd864362b84547c330b947c5
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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