4-(5-Chloro-3-nitropyridin-2-yloxy)phenol → 4-(3-Amino-5-chloropyridin-2-yloxy)phenol

HRID 845697Notes

Reaction equation

HRID 845697 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[H][H]>O1CCOCC1.[Ni]>[NH2:16][C:4]1[C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 201299744-(5-Chloro-3-nitropyridin-2-yloxy)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 201299724-(3-Amino-5-chloropyridin-2-yloxy)phenolYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

110.7 g (0.415 mole) of 4-(5-chloro-3-nitropyridin-2-yloxy)phenol are dissolved in 1200 ml of dioxan and, after addition of 22.0 g of Raney nickel catalyst, hydrogenated with hydrogen at 20°-25° C. The catalyst is then removed by filtration, the solution is concentrated and the residue is stirred in hexane and the product is filtered and dried, affording 96.0 g (98% of theory) of 4-(3-amino-5-chloropyridin-2-yloxy)phenol with a melting point of 174° C.

Workup

  1. customat 20°-25° C
  2. customThe catalyst is then removed by filtration
  3. concentrationthe solution is concentrated
  4. filtrationthe product is filtered
  5. customdried

Sources & evidence

ORD record
ord-c5e6b0b9e0be4f8f9ce40a0a6088dcc8
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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