Acetic Acid → HCID 86585757, compound

HRID 395743Notes

Reaction equation

HRID 395743 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[C:13]([NH:18]C(=O)C3C=CC=C(C#N)C=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[C:32]([OH:35])(=O)[CH3:33].O.[PH2]([O-])=O.[Na+]>N1C=CC=CC=1.[Ni]>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([N:11]([C:32](=[O:35])[C:33]2[CH:5]=[CH:6][CH:7]=[C:8]([C:9]#[N:11])[CH:29]=2)[C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10810822HCID 10810822, compoundHCID 178418950HCID 178418950, compound

Product 1

HCID 86585757HCID 86585757, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of N2-(4-tert-butylbenzoyl)-N1-(3-cyanobenzoyl)-1,2-benzenediamine (1.0 g, 2.5 mmol), water (25 mL), and acetic acid (25 mL) in pyridine (50 mL) was added sodium hypophosphite monohydrate (270 mg, 5.0 mmol) and Raney nickel (400 mg). The reaction mixture was heated at 45° C. for 3 h, cooled to room temperature, and filtered through diatomaceous earth. The filtrate was concentrated in vacuo and chromatographed (silica gel, 5% ethyl acetate/95% methylene chloride) to give 56 mg (6%) of the title compound as a white amorphous solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed (silica gel, 5% ethyl acetate/95% methylene chloride)

Sources & evidence

ORD record
ord-18d1495582254ea08c2bc4e30c96a102
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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