Hydrazine hydrate (1:1) → HCID 18174543, compound

HRID 427607Notes

Reaction equation

HRID 427607 reaction equation
C1(=O)[N:5]([C:6]2[N:11]=[C:10]([NH:12][C:13](=[O:33])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20][C:21](=[O:32])[C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[CH:9]=[CH:8][CH:7]=2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][C:6]1[N:11]=[C:10]([NH:12][C:13](=[O:33])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][C:21](=[O:32])[C:22]2[CH:23]=[CH:24][C:25]([C:28]([CH3:29])([CH3:31])[CH3:30])=[CH:26][CH:27]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18174536HCID 18174536, compound

Product 1

HCID 18174543HCID 18174543, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution N-(6-phthalimidopyridin-2-yl)-2-[(4-tert-butylbenzoyl)amino]benzamide (230 mg, 0.44 mmol) in ethanol (15 mL) was added hydrazine hydrate (0.22 g, 4.4 mmol). After refluxing the mixture for 30 min, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate, washed twice with saturated aqueous sodium bicarbonate solution, twice with saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in a minimal amount of chloroform and chromatographed (silica gel, eluting with a gradient of chloroform to 2% methanol/−98% chloroform. The appropriate fractions were combined and concentrated In vacuo to give 51 mg (30%) of the title compound as a white solid.

Workup

  1. temperatureAfter refluxing the mixture for 30 min
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed twice with saturated aqueous sodium bicarbonate solution, twice with saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in a minimal amount of chloroform
  9. customchromatographed (silica gel
  10. washeluting with a gradient of chloroform to 2% methanol/−98% chloroform
  11. concentrationconcentrated In vacuo

Sources & evidence

ORD record
ord-df4a849e23974b3e86ae97e0a1b169d3
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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