Ammonium Chloride → HCID 89239967, compound

HRID 593308Notes

Reaction equation

HRID 593308 reaction equation
[NH4+].[Cl-].[CH2:3]([C:6]1([CH2:26][O:27][CH3:28])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH:12]=2)[C:7]1=[O:25])[CH:4]=[CH2:5]>C(O)C.O.[Fe]>[CH2:3]([C:6]1([CH2:26][O:27][CH3:28])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)[CH:12]=2)[C:7]1=[O:25])[CH:4]=[CH2:5]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 89256210HCID 89256210, compound

Product 1

HCID 89239967HCID 89239967, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron powder (0.09 g, 1.7 mmol) and NH4Cl (0.023 g, 0.427 mmol) was added to a solution of 197F (0.3 g, 0.847 mmol) in 25 mL of ethanol-water (2:1) mixture. The reaction mixture was refluxed for 2 h, and solvent was removed under reduced pressure and extracted with ethyl acetate (40 mL). The organic layer was washed with water, dried over sodium sulphate, filtered and removed under reduced pressure to give title compound (0.22 g, %) as yellow solid. 1H NMR (300 MHz, DMSO-d6): 7.83 (d, J=8.4 Hz, 1H), 7.53-7.44 (m, 4H), 6.64 (d, J=9.0 Hz, 2H), 5.75-5.65 (m, 1H), 5.42 (s, 2H), 5.09-5.03 (m, 2H), 3.62 (d, J=9.0 Hz, 1H), 3.21 (s, 3H), 2.99-2.5 (m, 2H), 2.44-2.27 (m, 1H), 2.25-2.12 (m, 2H), 2.00-1.94 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customsolvent was removed under reduced pressure
  3. extractionextracted with ethyl acetate (40 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customremoved under reduced pressure

Sources & evidence

ORD record
ord-92cfa4630cf541cc8dc6a6aad96e1ec4
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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