Methyl 2-[4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy]propionate → HCID 20129973, compound

HRID 235556Notes

Reaction equation

HRID 235556 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:22]([O-])=O)[C:5]([O:8][C:9]2[CH:21]=[CH:20][C:12]([O:13][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[H][H]>O1CCOCC1.[Ni]>[NH2:22][C:4]1[C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:20][CH:21]=2)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 20129975Methyl 2-[4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy]propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 20129973HCID 20129973, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

190.8 g (0.541 mole) of methyl 2-[4-(5-chloro-3-nitropyridin-2-yloxy)phenoxy]propionate are dissolved in 1.9 l of dioxan. 40 g of Raney nickel catalyst are added and hydrogenation is effected with hydrogen at 20°-25° C. The catalyst is then removed by filtration, the solvent is distilled off and the still warm oily residue is crystallised by stirring it in hexane. The crystalline precipitate is isolated by filtration and dried, affording 167.4 g (96% of theory) of methyl 2-[4-(3-amino-5-chloropyridin-2-yloxy)phenoxy]propionate with a melting point of 92°-94° C.

Workup

  1. customThe catalyst is then removed by filtration
  2. distillationthe solvent is distilled off
  3. customthe still warm oily residue is crystallised
  4. customThe crystalline precipitate is isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-69156b65230d4d42beb8e714e2f3a4b7
Source dataset
uspto-grants-1987_02
Patent number
US04640703

Reaction notes

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