HCID 19733713, compound → HCID 11809022, compound

HRID 327767Notes

Reaction equation

HRID 327767 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1>[Ni].O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:21])[C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 19733713HCID 19733713, compound

Product 1

HCID 11809022HCID 11809022, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

20 g of Raney nickel catalyst are added to a solution of 196 g of 2-(4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy)propionic acid in 615 g of dioxane, and hydrogenation is subsequently carried out at 20°-22° C. under normal pressure. After separating the catalyst the solvent is removed, giving 98 g of 2-(4-(5-chloro-3-aminopyridin-2-yloxy)phenoxy)propionic acid as crude product (55% of theory) which has a melting point of 152°-154° C. and can be recrystallised from toluene.

Workup

  1. customis subsequently carried out at 20°-22° C. under normal pressure
  2. customAfter separating the catalyst the solvent
  3. customis removed

Sources & evidence

ORD record
ord-3280ea8de15e4cdc9a07ae6cea7c8645
Source dataset
uspto-grants-1993_12
Patent number
US05274100

Reaction notes

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