Pyruvic Acid → HCID 5183222, compound

HRID 489892Notes

Reaction equation

HRID 489892 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:12]([OH:17])(=[O:16])[C:13]([CH3:15])=O.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.S(=O)(=O)(O)O.[OH-].[NH4+]>C(O)(=O)C.O.C(Cl)(Cl)Cl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][CH:4]=1)[N:7]=[C:24]([C:23]1[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:28])[F:29])=[CH:27][CH:26]=1)[CH:15]=[C:13]2[C:12]([OH:17])=[O:16]

Participants

9

Reactant 5

HCID 1060Pyruvic AcidHCID 1118Sulfuric AcidHCID 99644-(Trifluoromethyl)anilineHCID 14923Ammonium HydroxideHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 5183222HCID 5183222, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-Trifluoromethylaniline (0.015 mmol, 1.88 mL), pyruvic acid (1.0 eq, 0.015 mmol, 2.04 mL) and 4-trifluoromethylbenzaldehyde were dissolved in acetic acid (10 mL). Concentrated sulfuric acid (10 mL) was cautiously added (exothermic) and stirred for 30 minutes. Chloroform (50 mL) and water (50 mL) were added followed by ammonium hydroxide until the solution was basic to pH paper. The layers were separated and the aqueous solution was extracted with chloroform (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and the solvent was evaporated under vacuum. The solid residue was purified by recrystallization from 95% ethanol to give the title compound as a yellow solid (580 mg, 10%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous solution was extracted with chloroform (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customThe solid residue was purified by recrystallization from 95% ethanol

Sources & evidence

ORD record
ord-b2f5bbf1b96c43f7b2a613ba17f430af
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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