Hydrochloric Acid → HCID 22618191, compound

HRID 842033Notes

Reaction equation

HRID 842033 reaction equation
[C:1]1([C:7]2[N:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>[Pd].CO.[OH-].[OH-].[Pd+2]>[C:1]1([CH:7]2[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:13][CH2:14][CH2:15][NH:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 10751082Methyl 2-phenylnicotinate

Product 1

HCID 22618191HCID 22618191, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-phenylnicotinate (9.43 g, 44.3 mmol) and palladium on carbon (10%; 2.5 g) in methanol (150 ml) containing hydrochloric acid (5M, 25 ml) was shaken for 72 hours under an atmosphere of hydrogen at 50 psi. Palladium hydroxide on carbon (20%; 1.0 g) was then added and hydrogenation resumed for a further 24 hours. A further portion of palladium hydroxide on carbon (1.0 g) was added, and hydrogenation continued for 24 hours more, until thin layer chromatography indicated no more starting material to be present. The suspension was filtered and evaporated to dryness, leaving the desired product as the hydrochloride salt. A small portion of this was basified with sodium carbonate to liberate the free base, isolated as a colourless oil. 1H NMR (360 MHz, CDCl3) δ 1.47-1.53 (1H, m), 1.78-1.90 (2H, m), 1.91-1.99 (1H, m), 2.81 (1H, dt, J 12.4, 2.9 Hz), 2.96-2.99 (1H, m), 3.31-3.36 (1H, m) 3.43 (3H, s), 3.95 (1H, d, J 3.4 Hz), 7.18-7.32 (5H, m).

Workup

  1. waithydrogenation resumed for a further 24 hours
  2. waithydrogenation continued for 24 hours
  3. filtrationThe suspension was filtered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-32c71be62dd745d2879d57cef84fa005
Source dataset
uspto-grants-2002_04
Patent number
US06372754B1

Reaction notes

Loading…