Ethanol → HCID 69002298, compound

HRID 1821327Notes

Reaction equation

HRID 1821327 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][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=2)=[N:2]1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)=[O:29]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 68998223HCID 68998223, compound

Product 1

HCID 69002298HCID 69002298, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Compound 64 (60 mg, 0.13 mmol), iron powder (364 mg, 6.50 mmol) and ammonium chloride (35 mg, 0.65 mmol) were added to 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 69 (11 mg, 22%).

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-16b36db4e8d740d3a4d37c486ec4068d
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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