Ethanol → HCID 59442944, compound

HRID 2380912Notes

Reaction equation

HRID 2380912 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[CH:14]=[CH:15][C:16]([N+:18]([O-])=O)=[CH:17][C:12]=3[O:11][C:10]([CH3:22])([CH3:21])[N:9]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:12]=3[O:11][C:10]([CH3:22])([CH3:21])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 59443042HCID 59443042, compound

Product 1

HCID 59442944HCID 59442944, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in (2) described above (2.2 g), reduced iron (2.0 g), ammonium chloride (780 mg), ethanol (40 mL) and water (10 mL) was heated under reflux for an hour. After cooling to room temperature, the reaction solution was filtered through Celite and the filtrate was concentrated in vacuo. Dichloromethane (50 mL) and water (50 mL) were added to the residue, and the aqueous layer was separated and extracted with dichloromethane (40 mL×2). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the titled compound (2.0 g) as a yellow powder, which was used in the next step without further purification.

Workup

  1. additionA mixture of the compound
  2. temperaturewas heated
  3. temperatureunder reflux for an hour
  4. filtrationthe reaction solution was filtered through Celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. additionDichloromethane (50 mL) and water (50 mL) were added to the residue
  7. customthe aqueous layer was separated
  8. extractionextracted with dichloromethane (40 mL×2)
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57b09e00005643ceb99011484d4e5b8e
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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