Ammonium Chloride → HCID 22936325, compound

HRID 387732Notes

Reaction equation

HRID 387732 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-])=O)=[CH:18][CH:17]=1.[Cl-].[NH4+]>C(O)C.O.O1CCCC1.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH2:30])=[CH:20][CH:21]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 22936764HCID 22936764, compound

Product 1

HCID 22936325HCID 22936325, compoundYield 56.93%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6,7-Dimethoxy-4-(4-(2-nitrophenylmethylamino)phenyloxy)quinoline (150 mg, 0.35 mmol) was dissolved in ethanol (2.8 ml) and water (0.7 ml), and then iron powder (78 mg, 1.4 mmol) and ammonium chloride (150 mg, 2.8 mmol) were added and the mixture was heated to reflux for 1 hour. After cooling to room temperature, the reaction solution was diluted with tetrahydrofuran and water, and the insoluble portion was filtered off. The filtrate was distilled off under reduced pressure, and then the residue was purified with a silica gel column (ethyl acetate system), the obtained amorphous substance was solidified with hexane and ethyl acetate, and the obtained crystals were washed with hexane-ethyl acetate, filtered out, washed with hexane and dried by aspiration at room temperature to obtain the title compound (80 mg, 0.1993 mmol, 56.93%) as milky white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationthe insoluble portion was filtered off
  4. distillationThe filtrate was distilled off under reduced pressure
  5. customthe residue was purified with a silica gel column (ethyl acetate system)
  6. washthe obtained crystals were washed with hexane-ethyl acetate
  7. filtrationfiltered out
  8. washwashed with hexane
  9. customdried by aspiration at room temperature

Sources & evidence

ORD record
ord-d70a4c226256450cbe00ca294103ebcb
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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