Ammonium Chloride → 6-Phenylpyridin-3-amine

HRID 1665640Notes

Reaction equation

HRID 1665640 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)([O-])=O>O.C1COCC1.[Zn]>[C:12]1([C:9]2[N:10]=[CH:11][C:6]([NH2:3])=[CH:7][CH:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 27628735-Nitro-2-phenylpyridine

Product 1

HCID 27628776-Phenylpyridin-3-amineYield 82.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (1.1 g, 0.020 mol) dissolved in water (15 mL) was added to a stirred solution of 5-nitro-2-phenyl-pyridine (0.5 g, 2.5 mmol) in THF (10 mL) Methanol (5 mL) was then added, affording a clear solution. Zinc powder (1.3 g, 0.020 mol) was then added portion wise at room temperature and the resulting mixture maintained for 1 hour, then filtered over celite. The filtrate was concentrated and the residue was extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 0.35 g (82%) of 6-phenyl-pyridin-3-ylamine. LCMS purity: 171.08 (M+1)+, 87.9%, 1H NMR (DMSO-d6): δ 8.12 (d, 1H), 8.0 (d, 2H), 7.72 (d, 1H), 7.48 (t, 2H), 7.36 (t, 1H), 7.1 (dd, 1H), 5.6 (s, 2).

Workup

  1. additionwas then added
  2. customaffording a clear solution
  3. temperaturethe resulting mixture maintained for 1 hour
  4. filtrationfiltered over celite
  5. concentrationThe filtrate was concentrated
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe organics were washed with brine solution
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88aa903d5cf2487da8df9bfaab65c75b
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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