Hydrochloric Acid → 6-(cyclopropylmethoxy)nicotinic acid

HRID 341506Notes

Reaction equation

HRID 341506 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]1([CH2:14][OH:15])[CH2:13][CH2:12]1.[OH-].[K+].Cl>CS(C)=O.O>[CH:11]1([CH2:14][O:15][C:2]2[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 75644CyclopropanemethanolHCID 792226-Chloronicotinic acid

Product 1

HCID 251165266-(cyclopropylmethoxy)nicotinic acidYield 88%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Chloropyridine-3-carboxylic acid (1.00 g, 6.347 mmol), cyclopropylmethanol (0.759 mL, 9.520 mmol) and potassium hydroxide (1.424 g, 25.39 mmol) were dissolved in DMSO (25 mL) and heated at 100 C for 18 h. The reaction mixture was cooled to room temperature; water was added and acidified to pH 4-5 with 1M hydrochloric acid. The resultant precipitate was filtered off under vacuum to afford the title compound (1.079 g, 88%). Method B HPLC-MS: MH+ requires m/z=193 Found: m/z=194, Rt=1.95 min (96%).

Workup

  1. temperatureheated at 100 C for 18 h
  2. filtrationThe resultant precipitate was filtered off under vacuum

Sources & evidence

ORD record
ord-86de564d3f584d75b0f84e0f1a7845fe
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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