Ammonium Chloride → HCID 21478799, compound

HRID 2292491Notes

Reaction equation

HRID 2292491 reaction equation
[Cl-].[NH4+].O.C(O)C.[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([N+:28]([O-])=O)=[C:19]([CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)C.[Fe]>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:28])=[C:19]([CH2:21][C:22]([O:24][CH:25]([CH3:26])[CH3:27])=[O:23])[CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 19096565Water ethanolHCID 19603840HCID 19603840, compound

Product 1

HCID 21478799HCID 21478799, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of ammonium chloride (5.63 g), a water/ethanol mixed solvent (1:1 v/v, 240 ml ) and powdery iron (29.3 g) was heated under reflux for one hour and a Soxhlet extractor containing isopropyl 5-benzyloxy-2-nitrophenylacetate was set and refluxing was continued for a further 3 hours and then allowed to stand at room temperature overnight. Insolubles were filtered off with Celite and the solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in ethyl ether, and the solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The oily substance thus obtained (18.9 g) was purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (10.8 g).

Workup

  1. temperatureunder reflux for one hour
  2. temperaturerefluxing
  3. waitto stand at room temperature overnight
  4. filtrationInsolubles were filtered off with Celite
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue thus obtained
  7. washthe solution was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe oily substance thus obtained (18.9 g)
  11. customwas purified by a silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1235d04ab90b40c59b380694378b3358
Source dataset
uspto-grants-1997_11
Patent number
US05684003

Reaction notes

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