Hydrochloric Acid → HCID 67366612, compound

HRID 1910961Notes

Reaction equation

HRID 1910961 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:6]([CH2:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)[CH:7]=[CH:8][CH:9]=1)=[O:4].[OH-:25].[Na+].Cl.[CH3:28]O>O>[O:22]=[C:11]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1)[CH2:10][N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:3]([O:4][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86657087HCID 86657087, compound

Product 1

HCID 67366612HCID 67366612, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a chilled (0° C.) solution of 2,2,2-trichloro-1-(1-{2-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)ethanone (105 mg, 0.26 mmol) in MeOH (7 mL) was added an aqueous solution of sodium hydroxide (1 M), (0.26 mL, 0.26 mmol). The solution was allowed at room temperature. After one hour the reaction was complete (monitored by LCMS). The mixture was acidified with 1 M HCl (aq), diluted with water (10 mL) and partially concentrated in vacuo to remove the MeOH. The aqueous mixture was then extracted with CH2Cl2 (3×4 mL). The organic layers were combined, dried (MgSO4), filtered and the filtrate concentrated in vacuo to yield methyl 1-{2-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]ethyl}-1H-pyrrole-2-carboxylate as a brown oil (85 mg, quantitative yield) ESI-MI m/z [M+H]+ 312.9.

Workup

  1. customwas allowed at room temperature
  2. concentrationpartially concentrated in vacuo
  3. customto remove the MeOH
  4. extractionThe aqueous mixture was then extracted with CH2Cl2 (3×4 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-4fac5d5a41e34d80abf8ff9c82264bac
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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