Ethanol → HCID 68996450, compound

HRID 1821326Notes

Reaction equation

HRID 1821326 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([C:21]2[S:22][C:23]([N+:27]([O-])=O)=[CH:24][C:25]=2[CH3:26])=[O:20])=[N:2]1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:27][C:23]1[S:22][C:21]([C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:20])=[C:25]([CH3:26])[CH:24]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 69000297HCID 69000297, compound

Product 1

HCID 68996450HCID 68996450, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

(E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-3-methyl-5-nitrothiophene-2-carboxamide (90 mg, 0.22 mmol), iron powder (621 mg, 11.13 mmol) and ammonium chloride (59 mg, 1.10 mmol) were added with ethanol (1.0 mL) and water (1.0 mL) at room temperature, stirred at 50° C. for 1 hour and then the reaction mixture was filtered through Celite. The filtrate was extracted with ethyl acetate and 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 ethyl acetate to obtain Compound 67 (26 mg, 32%).

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-9d17efa8a3a94b9e8714e16f7d799bd2
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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