Water → HCID 59477653, compound

HRID 570838Notes

Reaction equation

HRID 570838 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[C:10]([CH:11]=O)=[CH:9][N:8]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)[N:7]=2)[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2.Cl.[NH2:27]O.C([O-])=O.[Na+].O>C(O)=O>[S:1]1[CH:5]=[C:4]([C:6]2[C:10]([C:11]#[N:27])=[CH:9][N:8]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)[N:7]=2)[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 59477696HCID 59477696, compound

Product 1

HCID 59477653HCID 59477653, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 4-(3-benzo[b]thiophene-3-yl-4-formylpyrazole-1-yl)benzoic acid (0.26 g), hydroxylamine hydrochloride (0.058 g) and sodium formate (0.10 g) in formic acid (5 mL) was heated under reflux for 24 hours. To this reaction mixture was added water at room temperature, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. This obtained residue was dissolved with pyridine (5 mL), to this mixture was added trifluoroacetic anhydride (0.48 g) in a dropwise manner under ice cooling, and this mixture was stirred at room temperature for 5 hours. To this reaction mixture was added 2 mol/L hydrochloric acid, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was washed with n-hexane/diethyl ether=1/1 to give the title compound (0.13 g).

Workup

  1. temperatureunder reflux for 24 hours
  2. extractionthis mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. dissolutionThis obtained residue was dissolved with pyridine (5 mL), to this mixture
  7. additionwas added trifluoroacetic anhydride (0.48 g) in a dropwise manner under ice cooling
  8. additionTo this reaction mixture was added 2 mol/L hydrochloric acid
  9. extractionthis mixture was extracted with ethyl acetate
  10. washThis organic layer was washed with brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was removed under reduced pressure
  13. washThe obtained residue was washed with n-hexane/diethyl ether=1/1

Sources & evidence

ORD record
ord-14ab86b5a2584684a996d9e15d39b689
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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