Hydrochloric Acid → 2-Chloro-1-(4-methyl-3-pyridinyl)ethanone hydrochloride

HRID 1443369Notes

Reaction equation

HRID 1443369 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[ClH:11].CCOCC.Cl.[Cl:18]N1C(=O)CCC1=O>CCOCC.Cl.C(O)(=O)C>[ClH:18].[Cl:11][CH2:9][C:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 109424811-(4-Methyl-3-pyridinyl)ethanoneHCID 10953452Ether hydrochloride

Product 1

HCID 218649442-Chloro-1-(4-methyl-3-pyridinyl)ethanone hydrochlorideYield 83.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 22641269Acetate-hydrochloric acidSolvent

Procedure

In a 500 mL round bottom flask was piacea 1-(4-methyl-3-pyridinyl)ethanone (10.0 g, 74.1 mmol) in 90 mL of Et2O. To this solution was added 88.9 mL of 1M HCl/Et2O (1.2 eq, 88.9 mmol) with stirring and the solution allowed to stir for 1 h at room temperature, at which point, the precipitate was filtered and washed with Et2O. The solid was then dried in vacuo at about 60° C. This HCl salt (12. g, 70.0 mmol) was then dissolved in 70.0 mL of 1M HCl/acetic acid where 9.34 g (1 eq, 70.0 mmol) of N-chlorosuccinimide (NCS) was added and the reaction allowed to stir under Argon at room temperature overnight. At this point, 300 mL of Et2O was added resulting in an off-white precipitate. This was allowed to stir for 1 h at which point the solid was filtered and rinsed with Et2O to provide 12.0 g (83%) of the desired 2-chloro-1-(4-methyl-3-pyridinyl)ethanone hydrochloride. GC/MS RT=6.60 min; 1H-NMR (DMSO-d6) δ 2.51 (s, 3H), 5.15 (s, 2H), 7.68 (d, 1H), 8.68 (d, 1H), 9.06 (s, 1H); [M]+169 (95%).

Workup

  1. customIn a 500 mL round bottom flask was piacea
  2. stirringto stir for 1 h at room temperature, at which point
  3. filtrationthe precipitate was filtered
  4. washwashed with Et2O
  5. customThe solid was then dried in vacuo at about 60° C
  6. additionwas added
  7. stirringto stir under Argon at room temperature overnight
  8. customresulting in an off-white precipitate
  9. stirringto stir for 1 h at which point the solid
  10. filtrationwas filtered
  11. washrinsed with Et2O

Sources & evidence

ORD record
ord-c1163654c97847b8a8bef46d752fb2d6
Source dataset
uspto-grants-2010_02
Patent number
US07659412B2

Reaction notes

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