HCID 19837955, compound → HCID 19837954, compound

HRID 476563Notes

Reaction equation

HRID 476563 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:32])([CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(O)(=O)C.[Pd]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([N:20]2[CH2:21][CH2:22][N:17]([CH2:16][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])([OH:32])[CH2:10][N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[CH2:18][CH2:19]2)=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 19837955HCID 19837955, compound

Product 1

HCID 19837954HCID 19837954, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of the product of part (i) (0.55 g, 1.15 mmole) in acetic acid (20 ml) was added 10% palladium-on-charcoal (50 mg) and the mixture was hydrogenated at 15 psi (103 kPa) for 4 hours. The catalyst was then removed by filtration, the solvent removed under reduced pressure, and the residue partitioned between methylene chloride and water. The organic phase was separated, washed again with water, dried over magnesium sulphate and concentrated under reduced pressure to yield the title compound as a foam, m.p. 60° (0.485 g, 94%).

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe solvent removed under reduced pressure
  3. customthe residue partitioned between methylene chloride and water
  4. customThe organic phase was separated
  5. washwashed again with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f4c22da96e7484aabfcddf73192ca66
Source dataset
uspto-grants-1989_12
Patent number
US04885294

Reaction notes

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