Diethyl Ether → HCID 22482300, compound

HRID 2181798Notes

Reaction equation

HRID 2181798 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[CH2:15](OCC)[CH3:16]>>[CH2:15]([CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[NH:6]1)[CH3:16]

Participants

3

Reactant 2

HCID 3283Diethyl Ether2×HCID 9189Phenanthridine

Product 1

HCID 22482300HCID 22482300, compound

Procedure

A stirred solution of phenanthridine (25 g, 139 mmol) in anhydrous diethyl ether (100 mL) was cooled to −78° C., and treated drop-wise under nitrogen via syringe with a solution of 0.62 M ethyllithium1 in diethyl ether (225 mL, 139 mmol). The yellow solution was warmed to room temperature and stirred for three to four hours. The reaction was cooled to −78° C., and quenched with water. After warming to room temperature, the reaction mixture was extracted with diethyl ether, and the organic phase was washed sequentially with water and a saturated, aqueous, sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated in vacuo, to yield 6-ethyl-5,6-dihydrophenanthridine as a crude solid (26 g, 124 mmol, 89%).

Workup

  1. temperatureThe reaction was cooled to −78° C.
  2. customquenched with water
  3. temperatureAfter warming to room temperature
  4. extractionthe reaction mixture was extracted with diethyl ether
  5. washthe organic phase was washed sequentially with water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-4970da2577454dc4bcc32779fb452324
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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