Hydrochloric Acid → 6-(Cyclohexyloxy)-3-pyridinecarboxylic acid

HRID 341537Notes

Reaction equation

HRID 341537 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[OH-].[K+].[CH:13]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>CS(C)=O>[CH:13]1([O:19][C:2]2[N:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 14797Potassium HydroxideHCID 792226-Chloronicotinic acid

Product 1

HCID 167944166-(Cyclohexyloxy)-3-pyridinecarboxylic acidYield 55.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Chloronicotinic acid (0.500 g, 3.17 mmol), powdered potassium hydroxide (0.712 g, 12.69 mmol) and cyclohexanol (0.636 g, 6.35 mmol) were combined in DMSO (12 mL) and heated in a sealed tube to 100 C for 18 h and then to 120 C for 21 h. The mixture was acidified to pH 1 by adding 2M hydrochloric acid. The mixture was then left to stand at room temperature overnight and the resultant precipitate filtered off, washed with water and dried under vacuum to afford the title compound as a cream solid (0.389 g, 55%). 1H NMR (500 MHZ, MeOH-d4) δ ppm 8.76 (1H, d), 8.19 (1H, dd), 6.79 (1H, d), 5.11 (1H, m), 2.03 (2H, m), 1.83 (2H, m), 1.64 (1H, m), 1.56 (2H, m), 1.47 (2H, m) and 1.38 (1H, m).

Workup

  1. temperatureheated in a sealed tube to 100 C for 18 h
  2. waitThe mixture was then left
  3. waitto stand at room temperature overnight
  4. filtrationthe resultant precipitate filtered off
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3cf3347008c543fe83d23733599b4dc3
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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