Ethanol → HCID 23298115, compound

HRID 1953403Notes

Reaction equation

HRID 1953403 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]([N+:19]([O-])=O)[CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[NH2:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 23298101HCID 23298101, compound

Product 1

HCID 23298115HCID 23298115, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-[(E)-2-(6-acetamido-3-pyridyl)vinyl]nitrobenzene (3.0 g), iron powder (1.48 g) and ammonium chloride (0.57 g), ethanol (30 ml) and water (9 ml) was stirred under reflux for 5 hours. The reaction was filtered, concentrated and extracted with chloroform. The extracts were chromatographed on silica gel (20 g, chloroform-methanol 100:1 as eluent) to give an oil. Crystallization from methanol afforded 3-[(E)-2-(6-acetamido-3-pyridyl)vinyl]aniline (2.4 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. extractionextracted with chloroform
  5. customThe extracts were chromatographed on silica gel (20 g, chloroform-methanol 100:1 as eluent)
  6. customto give an oil
  7. customCrystallization from methanol

Sources & evidence

ORD record
ord-af891fd5e9ca4274ba1e12bd228268d9
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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