Hydrochloric Acid → HCID 13079850, compound

HRID 2418648Notes

Reaction equation

HRID 2418648 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].O.Cl>C(O)C.[Fe]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:11]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7]([CH3:21])=[N:8][CH:9]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13079822HCID 13079822, compound

Product 1

HCID 13079850HCID 13079850, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-Ethoxycarbonyl-2-methyl-5-(p-nitrophenyl)pyridine (2 g) was dissolved in warm ethanol (70 ml). Iron powder (4 g) was added to the solution followed by water (7 ml) containing 2 drops of 11.5 N-hydrochloric acid. The mixture was refluxed for 1.5 hours, cooled and filtered. The filtrate was concentrated and the residue dissolved in methylene dichloride. The solution was washed with water, dried and concentrated. The crude product was recrystallised from methylene dichloride-petroleum ether (b.p. 30°-40°) to give the title compound (1.23 g), m.p. 137°-8°.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue dissolved in methylene dichloride
  6. washThe solution was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe crude product was recrystallised from methylene dichloride-petroleum ether (b.p. 30°-40°)

Sources & evidence

ORD record
ord-70742ec6a7f8411fbb959eeea50b9df2
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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