Hydrochloric Acid → HCID 66276727, compound

HRID 341538Notes

Reaction equation

HRID 341538 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+].[F:13][C:14]([F:19])([F:18])[CH:15]([OH:17])[CH3:16].Cl>CS(C)=O>[F:13][C:14]([F:19])([F:18])[CH:15]([O:17][C:2]1[N:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][CH:10]=1)[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97741,1,1-Trifluoro-2-propanolHCID 14797Potassium HydroxideHCID 792226-Chloronicotinic acid

Product 1

HCID 66276727HCID 66276727, compoundYield 71%

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 1,1,1-trifluoropropan-2-ol (0.724 g, 6.35 mmol) were combined in DMSO (12 mL) and heated in a sealed tube to 100 C for 18 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 (0.527 g, 71%). 1H NMR (500 MHZ, MeOH-d4) δ ppm 8.82 (1H, d), 8.29 (1H, dd), 6.94 (1H, d), 5.96 (1H, m) and 1.52 (3H, d).

Workup

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

Sources & evidence

ORD record
ord-f56a4451e7644c6683bbd4835f5aa22b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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