Ammonium Chloride → 4-(5-Aminopyridin-2-yl)butanenitrile

HRID 1504965Notes

Reaction equation

HRID 1504965 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]#[N:14])=[N:8][CH:9]=1)([O-])=O.[NH4+].[Cl-]>O.CO.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]#[N:14])=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 682920074-(5-Nitropyridin-2-yl)butanenitrile

Product 1

HCID 682926344-(5-Aminopyridin-2-yl)butanenitrileYield 75%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of compound 77 (158 mg, 0.83 mmol), NH4Cl (666 mg, 12 mmol) and Iron Powder (463 mg, 8.3 mmol) in water (5 mL) and CH3OH (5 mL) was stirred at 90° C. for 1 h. After cooling, the reaction mixture was filtered and the solid was washed by DCM. The filtrates were separated, the organic layer was washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 78 (100 mg, 75%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ8.04 (s, 1H), 6.90-7.00 (m, 2H), 3.53 (br s, 2H), 2.83 (t, 2H, J=7.1 Hz), 2.36 (t, 2H, J=7.1 Hz), 2.02-2.12 (m, 2H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washthe solid was washed by DCM
  4. customThe filtrates were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0906691f588547bdab6a3bf7ac647005
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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