Hydrochloric Acid → HCID 54219358, compound

HRID 341846Notes

Reaction equation

HRID 341846 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.Cl>CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53734121HCID 53734121, compound

Product 1

HCID 54219358HCID 54219358, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

71 g of methyl 3-nitro-4-(3-pyridyloxy)benzoate and 52 g of iron powder are stirred in 500 ml of MeOH and, at RT, 500 ml of saturated aqueous HCl solution are slowly added. The mixture is then stirred at RT for 2 h and then the volatile constituents are removed in vacuo. The residue is stirred with 300 ml of saturated aqueous Na2CO3 solution (pH=11), and the precipitate is filtered off with suction. This precipitate is then extracted by boiling twice with 500 ml of EA each time, and the filtrate is extracted twice with 500 ml of EA each time. The combined EA phase is washed twice with 500 ml of water each time and dried over Na2SO4, and the solvent is removed in vacuo. 30 g of yellow-brown crystals, mp 101° C., are obtained.

Workup

  1. customthe volatile constituents are removed in vacuo
  2. stirringThe residue is stirred with 300 ml of saturated aqueous Na2CO3 solution (pH=11)
  3. filtrationthe precipitate is filtered off with suction
  4. extractionThis precipitate is then extracted
  5. extractionthe filtrate is extracted twice with 500 ml of EA each time
  6. washThe combined EA phase is washed twice with 500 ml of water each time
  7. dry with materialdried over Na2SO4
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6f4dfb6c81c34df993bd8c56de17f028
Source dataset
uspto-grants-1999_01
Patent number
US05856344

Reaction notes

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