Ammonium Chloride → HCID 86644284, compound

HRID 2265107Notes

Reaction equation

HRID 2265107 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1/[CH:11]=[C:12](\[CH3:18])/[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>O1CCCC1.CO.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1/[CH:11]=[C:12](\[CH3:18])/[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86644285HCID 86644285, compound

Product 1

HCID 86644284HCID 86644284, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 14c (17.3 g) was dissolved in tetrahydrofuran (180 ml) and methanol (180 ml), and iron powder (19.1 g) was added thereto. An ammonium chloride aqueous solution (1.67 mol/l, 110 ml) was added to the reaction mixture while refluxing under heating. The obtained mixture was refluxed under heating for 1 hour. After the mixture was allowed to cool, the iron powder was removed by Cerite filtration. Ethyl acetate and purified water were added to the filtrate, and extraction and washing were carried out. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized with n-heptane to obtain Compound 14d (13.0 g, 85%) as an opalescent solid.

Workup

  1. temperaturewhile refluxing
  2. temperatureunder heating
  3. temperatureThe obtained mixture was refluxed
  4. temperatureunder heating for 1 hour
  5. temperatureto cool
  6. customthe iron powder was removed by Cerite filtration
  7. customEthyl acetate and purified water
  8. additionwere added to the filtrate, and extraction
  9. washwashing
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe obtained residue was recrystallized with n-heptane

Sources & evidence

ORD record
ord-ea592dcb1b17406b8b18ebbc79950cf7
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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