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

HRID 845701Notes

Reaction equation

HRID 845701 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, compound

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 (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-52e2c7d309484b83aed8b3074f50ddb6
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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