Hydrochloric Acid → HCID 135434079, compound

HRID 2384371Notes

Reaction equation

HRID 2384371 reaction equation
Cl.[F:2][C:3]([F:34])([F:33])[C:4]1[CH:5]=[C:6]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:19]=[CH:18][C:17]=2[O:28]COC)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.C(=O)([O-])O.[Na+]>CO>[F:34][C:3]([F:2])([F:33])[C:4]1[CH:5]=[C:6]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:19]=[CH:18][C:17]=2[OH:28])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86595534HCID 86595534, compound

Product 1

HCID 135434079HCID 135434079, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (3 ml) and concentrated hydrochloric acid (0.5 ml) were added to N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxymethoxy-5-(pyridin-2-yl)benzamide (37.9 mg, 0.08 mmol), and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (16.2 mg, 47.2%) as a white powder.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washAfter the organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a54e2464b4ed417d8d485a51628ab73a
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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