Hydrochloric Acid → HCID 59354899, compound

HRID 341505Notes

Reaction equation

HRID 341505 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[OH:11][CH:12]1[CH2:16][CH2:15][O:14][CH2:13]1.[OH-].[K+].Cl>CS(C)=O>[O:14]1[CH2:15][CH2:16][CH:12]([O:11][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)[CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 99603-Furanol, tetrahydro-2×HCID 14797Potassium Hydroxide2×HCID 792226-Chloronicotinic acid

Product 1

HCID 59354899HCID 59354899, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 6-chloro-nicotinic acid (415 mg, 2.59 mmol), was added 3-hydroxytetrahydrofuran (468 mg, 5.16 mmol), potassium hydroxide (579 mg, 10.3 mmol) and DMSO (5 mL). The mixture was heated at 120 C for 24 h. Further potassium hydroxide (579 mg) and 3-hydroxytetrahydrofuran (468 mg) was added and the mixture heated at 120 C for 24 h. The reaction was allowed to cool to room temperature, acidified to pH=1-2 with a 2M aq. solution of HCl (13 mL) and extracted into EtOAc (3×5 mL). The combined extracts were washed with water (5×20 mL), saturated brine (2×20 mL) and dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the title compound as an orange solid which was dried under high vacuum to remove traces of solvent (209 mg, 39%). Method B HPLC-MS: MH+ requires m/z=210. Found: m/z=210, Rt=1.32 min (100%).

Workup

  1. temperatureThe mixture was heated at 120 C for 24 h
  2. temperaturethe mixture heated at 120 C for 24 h
  3. extractionextracted into EtOAc (3×5 mL)
  4. washThe combined extracts were washed with water (5×20 mL), saturated brine (2×20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f4385c1563e546e0a37d7d481efc84cb
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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