Sodium Hydroxide → HCID 21252834, compound

HRID 850800Notes

Reaction equation

HRID 850800 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13]3=[C:14]([C:16](=[O:19])[CH:17]=[CH:18][N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=3)[CH:15]=1)#[N:2].[OH-:20].[Na+]>C(OCCO)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:13]3=[C:14]([C:16](=[O:19])[CH:17]=[CH:18][N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=3)[CH:15]=1)(=[O:20])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 21252833HCID 21252833, compound

Product 1

HCID 21252834HCID 21252834, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

2-cyano-4H-pyrido[3,2,1-jk]carbazole-4-one (880 mg) produced in Example 173 was suspended in ethylene glycol monoethylether (88 ml), and 1N aqueous solution of sodium hydroxide (5.3 ml) was added to the suspension. The mixture was heated under reflux in an argon atmosphere for 4 hours, and allowed to cool. The reaction mixture was added to 2N aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate) to obtain the title compound (180 mg, 20%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an argon atmosphere for 4 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-9f9d552ca13848629d9704aea6445708
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

Loading…