Ammonium Chloride → 6-(benzyloxy)pyridin-3-amine

HRID 1665627Notes

Reaction equation

HRID 1665627 reaction equation
[Cl-].[NH4+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C1COCC1.[Fe]>[CH2:3]([O:10][C:11]1[N:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 2956762-benzyloxy-5-nitro-pyridine

Product 1

HCID 5632866-(benzyloxy)pyridin-3-amineYield 106.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Ammonium chloride (325 mg, 6.0 mmol) in water (10 mL) was added to a solution of 2-benzyloxy-5-nitro-pyridine (350 mg, 1.5 mmol) in THF (15 mL) and the resulting mixture stirred at 75° C. for 30 minutes. Iron powder (340 mg, 6 mmol) was then added portion wise and the mixture stirred for 5 hours at 75° C. The reaction mixture was filtered over celite. The filtrate was basified with sodium bicarbonate solution and the product extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and concentrated to afford 320 mg (100%) of 6-benzyloxy-pyridin-3-ylamine.

Workup

  1. stirringthe mixture stirred for 5 hours at 75° C
  2. filtrationThe reaction mixture was filtered over celite
  3. extractionthe product extracted with ethyl acetate
  4. washThe organics were washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0889fe27bb9f4c6da3ef0556bfbef9df
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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