Ammonium Chloride → HCID 57440938, compound

HRID 1819768Notes

Reaction equation

HRID 1819768 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([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:8]2)=[O:4].[NH4+].[Cl-]>CCO.C1COCC1.O.[Fe]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([O:15][C:16]1[C:17]([Cl:26])=[CH:18][C:19]([NH2:23])=[CH:20][C:21]=1[Cl:22])=[CH:8]2)=[O:4]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57440940HCID 57440940, compound

Product 1

HCID 57440938HCID 57440938, compoundYield 110.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of 3-(2,6-dichloro-4-nitro-phenoxy)-quinoline-6-carboxylic acid methyl ester (95) (0.93 mmol) and NH4Cl (283 mg, 5.3 mmol) in EtOH/THF/water (8 mL/16 mL/1 mL) was added iron powder (296 mg, 5.3 mmol). The reaction mixture was refluxed for 4 h. Insoluble materials were removed by Celite pad, which was washed by THF, acetone and then EtOH. The filtrate was concentrated, and sat NaHCO3 was added and extracted twice with AcOEt. Organic layer was washed by brine, dried over anhydrous MgSO4, and concentrated to afford compound 96 (372 mg, over weight). 1H NMR (300 MHz, DMSO-d6) δ 3.89 (3H, s), 5.75 (2H, s), 6.76 (2H, s), 7.73 (1H, d, J=2.9 Hz), 8.09 (2H, s), 8.67 (1H, s), 8.94 (1H, d, J=2.9 Hz).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customInsoluble materials were removed by Celite pad, which
  3. washwas washed by THF, acetone
  4. concentrationThe filtrate was concentrated
  5. additionwas added
  6. extractionextracted twice with AcOEt
  7. washOrganic layer was washed by brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-053f41a7e5cd4b6ca6ef45c80947a7e4
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

Loading…