Ethanol → HCID 69000070, compound

HRID 1821328Notes

Reaction equation

HRID 1821328 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](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)=[N:2]1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([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:29])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 69000912HCID 69000912, compound

Product 1

HCID 69000070HCID 69000070, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Compound 65 (60 mg, 0.13 mmol), iron powder (436 mg, 7.80 mmol) and ammonium chloride (42 mg, 0.78 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 ethanol to obtain Compound 70 (15 mg, 28%).

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 ethanol

Sources & evidence

ORD record
ord-55fc05329dc9463fbaec147f9b654bdd
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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