Water → HCID 55111360, compound

HRID 1808148Notes

Reaction equation

HRID 1808148 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12]O)=[CH:2]1.[Na].O>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([NH2:12])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 21763498HCID 21763498, compound

Product 1

HCID 55111360HCID 55111360, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1H-indol-3-yl)-1-phenylethanone-oxime (0.2 g, 0.75 mmol) dissolved in ethanol (10 ml) was mixed in portions with sodium pieces (500 mg, 21 mmol) in the boiling heat. This reaction mixture was stirred with reflux until the metal was fully dissolved. After cooling in an ice bath, water (15 ml) was carefully added to the reaction solution. The volatile constituents were then removed in a vacuum. The aqueous residue was extracted with ethyl acetate (3×30 ml). The combined organic phases were dried with sodium sulphate, filtered and all the volatile constituents removed in a vacuum. The residue (163 mg) obtained after distilling off the solvent was purified by column chromatography [silica gel 60 (30 g); methanol (500 ml)].

Workup

  1. temperatureboiling heat
  2. temperaturewith reflux until the metal
  3. dissolutionwas fully dissolved
  4. temperatureAfter cooling in an ice bath
  5. customThe volatile constituents were then removed in a vacuum
  6. extractionThe aqueous residue was extracted with ethyl acetate (3×30 ml)
  7. dry with materialThe combined organic phases were dried with sodium sulphate
  8. filtrationfiltered
  9. customall the volatile constituents removed in a vacuum

Sources & evidence

ORD record
ord-30c730e0d8924904a8b14c4a3f693a89
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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