Sodium Hydroxide → HCID 68997025, compound

HRID 1821332Notes

Reaction equation

HRID 1821332 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][N:16]=1)=[O:5].[Sn](Cl)Cl.[OH-].[Na+]>C(O)(=O)C.Cl>[NH2:28][C:26]1[CH:25]=[CH:24][C:3]([C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:13]=[CH:14]/[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][N:16]=2)=[O:5])=[C:2]([Cl:1])[CH:27]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 69002147HCID 69002147, compound

Product 1

HCID 68997025HCID 68997025, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

(E)-2-chloro-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-4-nitrobenzamide (60 mg, 0.14 mmol) was dissolved in acetic acid (1.0 mL) and hydrochloric acid (0.5 mL). The solution was added with tin(II) chloride (114 mg, 0.6 mmol), stirred at 40° C. for 2 hours, added with 6 mol/L sodium hydroxide to neutralize and then the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 84 (21 mg, 38%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-495a16448e2c486cb60c9b8ee24e5a7e
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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