Acetic Acid → HCID 21714308, compound

HRID 650062Notes

Reaction equation

HRID 650062 reaction equation
C(O)(=O)C.[CH3:5][N:6]([C:16]1[C:17]([N+:34]([O-])=O)=[C:18]([CH2:26][C:27](=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=1)[CH2:7][CH2:8][O:9]C1CCCCO1.Cl.N>C1(C)C=CC=CC=1.[Fe].C(OCC)(=O)C.O1CCCC1>[CH3:5][N:6]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]2[C:17]=1[NH:34][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26]2)[CH2:7][CH2:8][OH:9]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 53730400HCID 53730400, compound

Product 1

HCID 21714308HCID 21714308, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of iron powder (2.42 g, 43.3 mmol) and acetic acid (40 ml) was stirred at 70° C. Then, a solution of ethyl [3-[N-methyl-N-[2-(2-tetrahydro-2H-pyranyl)oxyethyl]amino]-2-nitro-6-trifluoromethylphenyl]pyruvate (2.00 g, 4.33 mmol) in toluene (20 ml) was added dropwise to the aforesaid mixture, followed by stirring at 78-83° C. for 2 hours. The reaction mixture was cooled to 30° C., after which 2N hydrochloric acid (20 ml) and tetrahydrofuran (20 ml) were added and the resulting mixture was stirred at room temperature for 2.5 hours. Subsequently, the reaction mixture was poured into an aqueous ammonia solution and ethyl acetate (300 ml) was added and then stirred. After being separated, the aqueous layer was extracted with ethyl acetate (200 ml) and the combined organic layer was washed with a 5% aqueous sodium chloride solution and then a 5% aqueous sodium hydrogencarbonate solution. The washed organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to obtain ethyl 7-[N-methyl-N-(2-hydroxyethyl)amino]-4-trifluoromethyl-1H-indole-2-carboxylate.

Workup

  1. stirringby stirring at 78-83° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to 30° C.
  3. stirringthe resulting mixture was stirred at room temperature for 2.5 hours
  4. additionwas added
  5. stirringstirred
  6. customAfter being separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (200 ml)
  8. washthe combined organic layer was washed with a 5% aqueous sodium chloride solution
  9. dry with materialThe washed organic layer was dried over anhydrous magnesium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent
  12. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-d6710531795a46d989935f9f5b766852
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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