Hydrochloric Acid → HCID 67365058, compound

HRID 1753161Notes

Reaction equation

HRID 1753161 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:6]([CH2:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:7]=[CH:8][CH:9]=1)=[O:4].[OH-:21].[Na+].O.Cl>O1CCOCC1>[O:18]=[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:10][N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:3]([OH:4])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67368224HCID 67368224, compound

Product 1

HCID 67365058HCID 67365058, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,2,2-trichloro-1-{1-[2-oxo-2-(pyridin-2-yl)ethyl]-1H-pyrrol-2-yl}ethanone (600 mg, 1.8 mmol) in 1,4-dioxane (20 ml) was added a solution of a aqueous solution of sodium hydroxide (1 M) (3.6 mL, 3.6 mmol) at 0° C. The mixture was allowed to warm to room temperature. After completion (30 minutes; reaction monitored by LCMS) water was added (40 mL). The mixture was then acidified with aqueous HCl (1 M) and extracted with EtOAc (3×40 mL). The organic layers were dried (Na2SO4), filtrated and concentrated in vacuo to give 1-[2-oxo-2-(pyridin-2-yl)ethyl]-1H-pyrrole-2-carboxylic acid as a pale brown solid that was used such as in the next step without purification (500 mg). ESI-MI m/z [M+H]+ 245.0.

Workup

  1. extractionextracted with EtOAc (3×40 mL)
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a82b30fabe04e5692a2770bb413e3ac
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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