Benzyl Alcohol → HCID 19437772, compound

HRID 1734531Notes

Reaction equation

HRID 1734531 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:16]1[N:17]=[N:18][CH:19]=[C:20]2[C:24]([N+:25]([O-:27])=[O:26])=[C:23]([CH3:28])[N:22]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:21]=12>CN1CCCC1=O>[CH2:1]([O:8][C:16]1[N:17]=[N:18][CH:19]=[C:20]2[C:24]([N+:25]([O-:27])=[O:26])=[C:23]([CH3:28])[N:22]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:21]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 19437767HCID 19437767, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19437772HCID 19437772, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

18.3 ml (177 mmol) of benzyl alcohol are added dropwise at room temperature to a solution of 33.0 g (295 mmol) of potassium tert-butoxide and 1.5 g (5.9 mmol) of [18]crown-6 in 180 ml of anhydrous N-methylpyrrolidone. The mixture is subsequently stirred at room temperature for a further 1 h. A solution of 15.9 g (59 mmol) of 7-chloro-1-isobutyl-2-methyl-3-nitropyrrolo[2,3-d]pyridazine in 50 ml of anhydrous N-methylpyrrolidone is then added dropwise in the course of 15 min. The suspension is then stirred at 80° C. for 2 h. After cooling to room temperature, it is treated with 400 ml of ice-water, and extracted with 3×300 ml of ethyl acetate. The organic extracts are washed with 3×200 ml of water and subsequently dried over magnesium sulfate. The residue which remains after concentration is chromatographed on silica gel (eluent: toluene/ethyl acetate=4:1). After concentration of the fractions of Rf=0.25 and crystallization from diisopropyl ether/ethyl acetate, 5.1 g (25%) of the title compound are isolated. M.p.: 162°-164° C.

Workup

  1. stirringThe suspension is then stirred at 80° C. for 2 h
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with 3×300 ml of ethyl acetate
  4. washThe organic extracts are washed with 3×200 ml of water
  5. dry with materialsubsequently dried over magnesium sulfate
  6. concentrationafter concentration
  7. customis chromatographed on silica gel (eluent: toluene/ethyl acetate=4:1)
  8. customAfter concentration of the fractions of Rf=0.25 and crystallization from diisopropyl ether/ethyl acetate, 5.1 g (25%) of the title compound
  9. customare isolated

Sources & evidence

ORD record
ord-8a67e755d3094a64b5694a4ed89c3ee0
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

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