Hydrazine → HCID 86598464, compound

HRID 1745900Notes

Reaction equation

HRID 1745900 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[N+:26]([O-])=O)[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2].NN>C(O)C.C1COCC1.[Pd]>[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH:17][C:18]1[C:19]([NH2:26])=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 9321HydrazineHCID 22042246HCID 22042246, compound

Product 1

HCID 86598464HCID 86598464, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

([8-(tert-Butyl-dimethyl-silanyloxy)-quinolin-2-yl]-(4-methoxy-2-nitro-phenyl)-amine 1B (21.9 g, 51.3 mMol) was dissolved in a solution of 200 mL ethanol (EtOH) and 70 mL of THF under an atmosphere of dry N2. To this solution was added 10% palladium on carbon (2.18 g) followed by the dropwise addition of 10 mL of anhydrous hydrazine. The reaction mixture was stirred at ambient temperature for 2 hours after which time it was filtered through Celite™ and the Celite™ was washed with DCM. The combined filtrates were concentrated under vacuum and the resulting residue was partitioned between DCM and aqueous saturated NaHCO3. The DCM layer was then washed again with saturated NaHCO3 and then brine, dried over Na2SO4, filtered and concentrated under vacuum to give 18.3 g of a tan solid as the title compound 1C.

Workup

  1. filtrationwas filtered through Celite™
  2. washthe Celite™ was washed with DCM
  3. concentrationThe combined filtrates were concentrated under vacuum
  4. customthe resulting residue was partitioned between DCM and aqueous saturated NaHCO3
  5. washThe DCM layer was then washed again with saturated NaHCO3
  6. dry with materialbrine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bcd44b8765fd4cee9b8369e5113aaa61
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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