Triethylamine → 6-Propylnicotinic acid

HRID 710473Notes

Reaction equation

HRID 710473 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=1)#[C:2][CH3:3].C(N(CC)CC)C>CCO.[Pd]>[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 667263446-(Prop-1-yn-1-yl)nicotinic acid

Product 1

HCID 190793426-Propylnicotinic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of Step A (0.25 g; 1.55 mmol), 10% Pd/C (0.15 g) and triethylamine (0.5 ml) in EtOH (15 ml) was stirred overnight at room temperature under H2 (Parr apparatus; 100 psi). The catalyst was removed by filtration, washed with fresh EtOH (2×10 ml), and combined filtrates were evaporated to dryness to give the title compound (0.25 g; 100%), as greyish solid, which was used in the next Step without further purification. 1H-NMR (CDCl3) 0.94 (tr, 3H, J=6 Hz); 1.69-1.81 (m, 2H); 2.83 (tr, 2H, J=6 Hz); 7.2 (d, 1H, J=9 Hz); 8.19 (s, 1H); 8.28 (d, 1H, J=9 Hz); 10.65 (broad s, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with fresh EtOH (2×10 ml)
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-b49275a762c24e05ba452ad5bb853610
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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