Ammonium Chloride → 3-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl ester

HRID 1865549Notes

Reaction equation

HRID 1865549 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([N+:23]([O-])=O)=[CH:18][C:17]=1[Cl:26])=[CH:10]2)=[O:4].[NH4+].[Cl-]>CCO.C1COCC1.O.[Fe]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:17]([Cl:26])=[CH:18][C:19]([NH2:23])=[CH:20][C:21]=1[Cl:22])=[CH:10]2)=[O:4]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 574409423-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

Product 1

HCID 574409393-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl esterYield 118.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of 3-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester (314) (1.26 mmol) and NH4Cl (370 mg, 6.91 mmol) in EtOH/THF/H2O=8 ml/4 ml/2 ml was added Iron powder (386 mg, 6.91 mmol). The reaction mixture was refluxed for 3.5 hr. After cooling to room temperature and insoluble materials were filtered by Celite filtration. The filtrate was concentrated and sat NaHCO3 was added to the residue, which was extracted twice with AcOEt. Organic layer was washed by Brine, dried over MgSO4, and concentrated. Crude residue was purified by column chromatography (Hexane/AcOEt=2/1, 80 g of silica gel) to afford compound 315 (543 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 3.5 hr
  2. filtrationinsoluble materials were filtered by Celite filtration
  3. concentrationThe filtrate was concentrated
  4. additionwas added to the residue, which
  5. extractionwas extracted twice with AcOEt
  6. washOrganic layer was washed by Brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customCrude residue was purified by column chromatography (Hexane/AcOEt=2/1, 80 g of silica gel)

Sources & evidence

ORD record
ord-3e3c6daef61c4f5294c915c4fd0e629c
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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