Hydrochloric Acid → (2',3-Dimethyl-[2,4'-bipyridin]-5-yl)methanamine hydrochloride

HRID 711288Notes

Reaction equation

HRID 711288 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH:15]=[N:16]O)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[ClH:18]>[Pd].C(O)C>[ClH:18].[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][NH2:16])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1363597592',3-Dimethyl-[2,4'-bipyridine]-5-carbaldehyde oxime

Product 1

HCID 66632693(2',3-Dimethyl-[2,4'-bipyridin]-5-yl)methanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 2-L Parr-Shaker Reactor was charged 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde oxime (34f, 560 mmol), Pd/C (23 g, 112 mmol, 50 wt % wet), conc. HCl (94 mL), and ethanol (600 mL). The reaction mixture was shaked at rt under 40 psi H2 until H2 was consumed. After filtration through Celite, the filtrate was solvent-exchanged to ethanol by repeating the concentration and refilling with ethanol twice. The product was stirred in ethanol/iso-propyl acetate (800 mL, v 1/1) at rt for 18 h. The solid was collected by filtration and rinsed with EtOH/iso-propyl acetate (400 mL, v 1/1). The wet cake was dried at 50° C. under vacuum for 18 h to afford (2′,3-dimethyl-[2,4′-bipyridin]-5-yl)methanamine hydrochloride (34g) as a light yellow powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.44 (s, 3H), 2.89 (s, 3H), 4.15 (q, J=5 Hz, 2H), 8.05 (dd, J=1.6, 6.0 Hz, 1H), 8.10 (d, J=1.6 Hz, 1H), 8.13 (s, 1H), 8.76 (d, J=2.0 Hz, 1H), 8.85 (d, J=6.0 Hz, 1H), 8.88 (brd, 3H).

Workup

  1. customwas shaked at rt under 40 psi H2 until H2
  2. customwas consumed
  3. filtrationAfter filtration through Celite
  4. concentrationthe concentration
  5. filtrationThe solid was collected by filtration
  6. washrinsed with EtOH/iso-propyl acetate (400 mL, v 1/1)
  7. customThe wet cake was dried at 50° C. under vacuum for 18 h

Sources & evidence

ORD record
ord-1a993db60b754f64944fc616f586a78e
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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