Sodium Hydroxide → HCID 45275137, compound

HRID 1622350Notes

Reaction equation

HRID 1622350 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:15])[C:7]=1[N:8]1[CH2:12][CH2:11][CH:10]([C:13]#[N:14])[CH2:9]1.[OH-:16].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:15])[C:7]=1[N:8]1[CH2:12][CH2:11][CH:10]([C:13]([NH2:14])=[O:16])[CH2:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58378288HCID 58378288, compound

Product 1

HCID 45275137HCID 45275137, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(3,5-dichloropyridin-4-yl)pyrrolidine-3-carbonitrile 14 (83 mg, 0.34 mmol) in sulphuric acid (3 mL) was stirred for 90 min and then poured onto ice/water (100 g). The mixture was made basic by the addition of a 2 M solution of sodium hydroxide and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried (MgSO4) and concentrated under reduced pressure, to furnish the title compound as a white solid (65 mg, 73%), m.p. 161-163° C.; umax (CHCl3)/cm−1 3053, 2985, 1689, 1558, 1465; m/z (ESI) C10H12Cl2N3O requires 260.0352 found [M+H]+ 260.0355.

Workup

  1. additionpoured onto ice/water (100 g)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-222490b757d24fbaa6f0374a334622ee
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

Loading…