Hydrochloric Acid → 4-Chloro-2-(pyrrolidine-1-carbonyl)pyridine

HRID 1993535Notes

Reaction equation

HRID 1993535 reaction equation
CO[C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][N:6]=1)=[O:4].[Mg+2].[Cl-].[Cl-].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.Cl>C1COCC1.C(OCC)(=O)C>[Cl:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:3]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:4])[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 820890Methyl 4-ChloropicolinateHCID 5360315Magnesium Chloride

Product 1

HCID 106799924-Chloro-2-(pyrrolidine-1-carbonyl)pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-pyridine-2-carboxylic acid methylester (200 mg, 1.17 mmol) and MgCl2 (555 mg, 0.58 mmol) are suspended in THF (5 mL) at rt. The mixture is stirred for 5 min and then pyrrolidine (193 μL, 2.33 mmol) is added and the mixture stirred for an additional 15 min. It is worked up by addition of aqueous HCl solution (1M, 1.2 mL) and extraction with ethyl acetate. The combined organic extracts are washed with brine dried over MgSO4. The volatiles are removed under reduced pressure to give the title compound as a yellow oil: C10H11ClN2O: M+=211.3; 1H-NMR (DMSO-d6): 8.55 (d, 1H), 7.82 (s, 1H), 7.59 (d, 1H), 3.62-3.42 (m, 4H), 1.93-1.75 (m, 4H).

Workup

  1. stirringthe mixture stirred for an additional 15 min
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. customThe volatiles are removed under reduced pressure

Sources & evidence

ORD record
ord-f8386c10cd1d4509a78d7a1f2f7782c0
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…