Ammonia → 6-Phenoxy-3-pyridinamine

HRID 1633914Notes

Reaction equation

HRID 1633914 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O.C(=O)([O-])[O-].[Na+].[Na+].N>Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 32523715-Nitro-2-phenoxypyridine

Product 1

HCID 2128566-Phenoxy-3-pyridinamineYield 70%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
20 °C

Procedure

5-Nitro-2-phenoxypyridine (0.5 9, 2.3 mmol) was added portion wise to a solution of stannous chloride (2.6 g, 12 mmol) dissolved in concentrated hydrochloric acid (10 mL) at a temperature of 0-5° C. The reaction mixture was then stirred at 20° C. for 16 hours. Sodium carbonate (5 g) and aqueous ammonia (50 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL) and the combined organic phases were washed with water (2×40 mL), dried (MgSO4), and concentrated in vacuo to give 0.3 g of 5-amino-2-phenoxypyridine.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  2. washthe combined organic phases were washed with water (2×40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-707db58e465d46b1b7ed57dd2889d1cf
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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