Water → HCID 19701558, compound

HRID 862090Notes

Reaction equation

HRID 862090 reaction equation
[Cl:1][C:2]1[C:3]([CH:11]([C:23]#[N:24])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH2:20][O:21][CH3:22])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.O>C(O)(=O)C.[Fe]>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([CH:11]([C:23]#[N:24])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH2:20][O:21][CH3:22])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19701601HCID 19701601, compound

Product 1

HCID 19701558HCID 19701558, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

In acetic acid (300 ml) was dissolved 3-chloro-2-(5-chloro-a-cyano-2-methoxymethoxybenzyl)-5-nitropyridine (15.0 g). To the solution were added water (10 ml) and powdery iron (11.4 g). The mixture was stirred for 2 hours at room temperature. The solvent was distilled off under reduced pressure. To the residue were added ethyl acetate and an aqueous solution of sodium carbonate. Insolubles were filtered off by using celite. The organic layer was washed with water and a saturated aqueous saline solution, successively, which was then dried (anhydrous magnesium sulfate), followed by concentration. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to afford 5-amino-3-chloro-2-(5-chloro-α-cyano-2-methoxymetho-xybenzyl)pyridine (12.4 g) (Compound D-13). Physico-chemical properties and spectrum data are shown in Table 13 and Table 15.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionTo the residue were added ethyl acetate
  3. filtrationInsolubles were filtered off
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous saline solution, successively, which was then dried (anhydrous magnesium sulfate)
  6. concentrationfollowed by concentration
  7. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-486e39a15369439ead6824914c995ca4
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

Loading…