2-(4-Chlorophenoxy)-5-nitropyridine → 6-(4-chlorophenoxy)pyridin-3-amine

HRID 1156210Notes

Reaction equation

HRID 1156210 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 2771852-(4-Chlorophenoxy)-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 4206446-(4-chlorophenoxy)pyridin-3-amineYield 94.2%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Chlorophenoxy-5-nitropyridine (19.9 g) and platinum dioxide (0.1 g) were suspended in a mixture of tetrahydrofuran (100 ml) and ethyl acetate (50 ml), and catalytic reduction was carried out until 5.0 liters of hydrogen were absorbed. After removal of the catalyst by filtration, the solvent was distilled out under reduced pressure. The precipitated crystals were washed with a small amount of ether to give 16.5 g of 4-chlorophenoxy-5-aminopyridine as white crystals. M.P., 87°-88° C.

Workup

  1. customwere absorbed
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. distillationthe solvent was distilled out under reduced pressure
  5. washThe precipitated crystals were washed with a small amount of ether

Sources & evidence

ORD record
ord-17fe63a8741e42b2941a15393552ca86
Source dataset
uspto-grants-1982_06
Patent number
US04334912

Reaction notes

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