tert-butyl N'-(quinolin-2-yl)methylene-hydrazinecarboxylate → HCID 69200678, compound

HRID 746380

Reaction equation

HRID 746380 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[N:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CO.[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 1

HCID 69201455tert-butyl N'-(quinolin-2-yl)methylene-hydrazinecarboxylate

Product 1

HCID 69200678HCID 69200678, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.5 g 10% Pd/C are added to a solution of 15.00 g tert-butyl N′-(quinolin-2-yl)methylene-hydrazinecarboxylate in 200 ml of methanol. The resulting mixture is then shaken for 6 h at ambient temperature under 1 atm H2 pressure. Then the precipitate and the catalyst are separated from the solvent, the precipitate is dissolved in tetrahydrofuran, filtered again and in this way the catalyst is separated off. The THF solution is evaporated down and the residue is triturated with tert-butylmethylether, separated off and dried at 50° C. The tert-butylmethylether phase is evaporated down again and the residue is triturated this time with diethyl ether, separated off and dried at 50° C. The two solid fractions from the purification with tert-butylmethylether and diethyl ether are combined.

Workup

  1. customThen the precipitate and the catalyst are separated from the solvent
  2. dissolutionthe precipitate is dissolved in tetrahydrofuran
  3. filtrationfiltered again and in this way the catalyst
  4. customis separated off
  5. customThe THF solution is evaporated down
  6. customthe residue is triturated with tert-butylmethylether
  7. customseparated off
  8. customdried at 50° C
  9. customThe tert-butylmethylether phase is evaporated down again
  10. customthe residue is triturated this time with diethyl ether
  11. customseparated off
  12. customdried at 50° C
  13. customThe two solid fractions from the purification with tert-butylmethylether and diethyl ether

Sources & evidence

ORD record
ord-4fcf1674b04f436da8dfa007a169f5a3
Source dataset
uspto-grants-2008_07
Patent number
US07393847B2

Linked notes

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