HCID 23368094, compound → HCID 19706203, compound

HRID 1647331Notes

Reaction equation

HRID 1647331 reaction equation
[N:1]([CH:4]([CH:12]([OH:26])[CH:13]([OH:25])[CH:14]([N:22]=[N+]=[N-])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][CH:4]([CH:12]([OH:26])[CH:13]([OH:25])[CH:14]([NH2:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 23368094HCID 23368094, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19706203HCID 19706203, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 67 mg (0.19 mmol) of 6 in 4 mL of methanol was stirred with 30 mg of 10% palladium on carbon under 1 atmospheric hydrogen pressure for 18 hours at room temperature. The mixture was filtered through a 0.45 micron Millipore filter and the residue washed with methanol. The filtrate and the washings were concentrated to provide 45 mg (79% yield) of 7. This material showed NMR (CDCl3): d 2.64 (m, 8H), 7.283 (m, 10H).

Workup

  1. filtrationThe mixture was filtered through a 0.45 micron Millipore
  2. filtrationfilter
  3. washthe residue washed with methanol
  4. concentrationThe filtrate and the washings were concentrated

Sources & evidence

ORD record
ord-9176a7606f044da1b07716fe04fc1533
Source dataset
uspto-grants-1995_07
Patent number
US05430155

Reaction notes

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