Hydrochloric Acid → HCID 67366612, compound

HRID 1753183Notes

Reaction equation

HRID 1753183 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-715b7798c97f4bd6aa0a631527c0a766
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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