Hydrochloric Acid → (2-Fluoropyridin-3-yl)methanamine hydrochloride

HRID 736989Notes

Reaction equation

HRID 736989 reaction equation
[ClH:1].[F:2][C:3]1[N:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6]>CO.[Pd]>[ClH:1].[F:2][C:3]1[C:4]([CH2:5][NH2:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27832543-Cyano-2-fluoropyridine

Product 1

HCID 67023208(2-Fluoropyridin-3-yl)methanamine hydrochlorideYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add concentrated HCl (0.46 mL) to a suspension 2-fluoro-nicotinonitrile (0.34 g, 2.8 mmol) and 5% Pd/C (0.5 g) in methanol (10 mL) at RT. Stir suspension under an atmosphere of hydrogen at 1 atm. For 6 hours. Filter reaction mixture and concentrate the filtrate. Add ether to the residue, bubble HCl gas through the suspension, filter precipitate, and dry to give the title compound (0.37 g, 82%). MS (ES) 127.1 (M+1)+. 1H NMR (400 MHz, DMSO) δ: 8.65 (brs, 3H), 8.24 (m, 1H), 8.16 (m, 1H), 7.41 (m, 1H), 4.06 (m, 2H).

Workup

  1. filtrationFilter
  2. customreaction mixture
  3. concentrationconcentrate the filtrate
  4. customAdd ether to the residue, bubble HCl gas through the suspension
  5. filtrationfilter precipitate
  6. customdry

Sources & evidence

ORD record
ord-11454c6edbf0444f913b2dba4c05b24b
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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