Hydrochloric Acid → HCID 68732791, compound

HRID 2068695Notes

Reaction equation

HRID 2068695 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[OH-].[K+].[CH3:11][N:12]([CH2:14][CH2:15]Cl)[CH3:13].Cl>CS(C)=O.O>[Br:8][C:6]1[CH:5]=[CH:4][N:3]([CH2:15][CH2:14][N:12]([CH3:13])[CH3:11])[C:2](=[O:1])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79012-Chloro-N,N-dimethylethylamineHCID 14797Potassium HydroxideHCID 178515446HCID 178515446, compound

Product 1

HCID 68732791HCID 68732791, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-hydroxy-4-bromopyridine (0.10 g, 0.57 mmol) in DMSO (1.0 mL) was added KOH (0.13 g, 2.29 mmol) and the resulting reaction mixture was stirred for 10 min at room temperature followed by addition of N,N-dimethylaminoethylchloride.HCl (0.098 g, 0.68 mmol). The reaction mixture was then stirred at 40° C. for 1 h. After the completion of reaction (TLC monitoring), water was added to the reaction and extracted with EtOAc (3×25 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was triturated with ether to obtain the desired product (0.10 g, 72%). MS: 245.10 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. stirringThe reaction mixture was then stirred at 40° C. for 1 h
  3. additionwas added to the reaction
  4. extractionextracted with EtOAc (3×25 mL)
  5. washThe combined organics was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-802c212308ea40dcb15be69b28a82ae8
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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