Hydrochloric Acid → (5-Chloropyridin-2-yl)methanamine

HRID 1664155Notes

Reaction equation

HRID 1664155 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.Cl>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 38339425-Chloro-2-cyanopyridine

Product 1

HCID 21069929(5-Chloropyridin-2-yl)methanamineYield 51.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-chloropicolinonitrile (3.8 g, 27.43 mmol), conc. HCl (3 mL) and 10% Pd—C (1.0 g) in ethanol (100 mL) was shaken under a hydrogen atmosphere (40 psi) for 2 h. The reaction mixture was filtered, concentrated and the resulting residue taken up in satd NaHCO3 (50 mL) and extracted with CH2Cl2 (4×25 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give the title compound as a yellow oil (2.0 g, 51% yield). LCMS (M+H) calcd for C6H8ClN2: 143.04; found: 143.07. 1HNMR (500 MHz, CDCl3) δ ppm: 8.56-8.51 (1H, br d), 7.66-7.60 (1H, m), 7.28-7.14 (1H, m), 3.97 (2H, s), 1.72 (2H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. extractionextracted with CH2Cl2 (4×25 mL)
  4. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1acfa9c5284045ffb6d92616da32d3f8
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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