Water → HCID 22269797, compound

HRID 488523Notes

Reaction equation

HRID 488523 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].O>CN(C=O)C.CC#N.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 962WaterHCID 22269765HCID 22269765, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22269797HCID 22269797, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-{4-[3-(4-nitrophenyl)propyl]phenylamino}benzoic acid (Example 158) (3.0 g, 7.97 mmol) in DMF (40 mL) was added 10% Pd—C (300 mg) at room temperature under argon atmosphere. Hydrogen gas (1 atm) was introduced into the flask and the mixture was stirred for 14 hours at room temperature. The reaction mixture was filtered through a Celite pad to remove Pd—C and concentrated in vacuo. The residue was diluted with MeOH (ca. 50 mL) and concentrated in vacuo. This operation was repeated 3 times to remove any trace of DMF. The residue was diluted with McOH again, and insoluble stuff was removed by filtration. Removing the solvent of the filtrate in vacuo afforded an oil, which was diluted with CH3CN (50 mL) and added dropwise water (100 mL) slowly. The precipitate formed was filtered and dried at 60° C. in vacuo, affording the title compound as a white solid (2.34 g, 85% yield). mp 110-112° C. MS (Fab): 347 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. customto remove Pd—C
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with MeOH (ca. 50 mL)
  5. concentrationconcentrated in vacuo
  6. customto remove any trace of DMF
  7. additionThe residue was diluted with McOH again
  8. custominsoluble stuff was removed by filtration
  9. customRemoving the solvent of the filtrate in vacuo
  10. customafforded an oil, which
  11. customThe precipitate formed
  12. filtrationwas filtered
  13. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-a88d68ebdcbd4a3181c407263d0def15
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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