3-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine → 3-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine

HRID 1426166Notes

Reaction equation

HRID 1426166 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-])=O)=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.ClCCl.[Zn]>[CH2:1]([O:8][C:9]1[C:10]([NH2:23])=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 673694033-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine

Product 1

HCID 673705813-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amineYield 98.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Zinc (1.34 g, 20.5 mmol) was added slowly to a solution of 3-(benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine (0.730 g, 2.05 mmol) in acetic acid (20 mL) in a water bath. The reaction mixture was stirred 2 hours, then diluted with dichloromethane (100 mL) and filtered through Celite. The pad was washed several times with dichloromethane, and the combined filtrates were concentrated. The residue was partitioned between ethyl acetate and 2N NaOH, and the organic layer was washed with brine, dried, and concentrated to afford 3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine (0.66 g, 98.7% yield) as a light yellow oil. 1H NMR (CDCl3) δ 4.85 (bs, 2H), 5.03 (s, 2H), 6.79-6.83 (m, 2H), 7.02 (t, 1H), 7.14 (t, 1H), 7.37-7.47 (m, 7H).

Workup

  1. filtrationfiltered through Celite
  2. washThe pad was washed several times with dichloromethane
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was partitioned between ethyl acetate and 2N NaOH
  5. washthe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1656dbb393d24203a6b5c7cd91069b6a
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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