HCID 15541328, compound → HCID 15541329, compound

HRID 1721317Notes

Reaction equation

HRID 1721317 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[CH3:17])[CH2:4][CH2:3]1>C(O)C.[Pd].C(O)C.O.ClCCl>[CH3:17][C:9]1[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:8]=1[N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1

Participants

6

Reactant 1

HCID 15541328HCID 15541328, compound

Product 1

HCID 15541329HCID 15541329, compoundYield 103.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of the product of step (a) (4.5 g) in ethanol was added under vacuum to a prehydrogenated suspension of palladium on charcoal (10% Pd on C, 50% paste with water, 1.4 g) in ethanol:water (5:2., 50 ml). The suspension was stirred at room temperature under an atmosphere of hydrogen for 2 hours. The suspension was filtered through a pad of hyflo, the filter pad washed well with ethanol:water (4:1,200 ml) and the combined filtrates evaporated in vacuo to give a gummy solid which was dissolved in dichloromethane, dried and concentrated in vacuo to give the title compound as a pale green crystalline solid (4.052 g) m.p. 82°-83° C. Analysis Found: C, 70.2; H, 9.5; N,20.4 C12H19N3 requires: C, 70.2; H, 9.3; N, 20.5%

Workup

  1. filtrationThe suspension was filtered through a pad of hyflo
  2. washthe filter pad washed well with ethanol
  3. customwater (4:1,200 ml) and the combined filtrates evaporated in vacuo
  4. customto give a gummy solid which
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ce2d81b4b4342f0a4c9c5bffad5118f
Source dataset
uspto-grants-1996_04
Patent number
US05510350

Reaction notes

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