Hydrochloric Acid → HCID 11796274, compound

HRID 395780Notes

Reaction equation

HRID 395780 reaction equation
[NH2:1][C:2](=[N:31]O)[C:3]1[CH:4]=[C:5]([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:6]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1.O1CCCC1.Cl.[H][H]>C(O)C.[Pd].O>[NH2:31][C:2](=[NH:1])[C:3]1[CH:4]=[C:5]([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:6]([NH:9][C:10](=[O:19])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 54488891HCID 54488891, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11796274HCID 11796274, compoundYield 35.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution 4-[(amino)(hydroxyimino)methyl]-N1,N2-bis(4-methoxybenzoyl)-1,2-benzenediamine (0.50 g, 1.2 mmol), tetrahydrofuran (5 mL), water (25 mL), and 1 N aqueous hydrochloric acid (1.4 mL) in ethanol (50 mL) was added 10% palladium-on-carbon (250 mg). The vessel was placed under vacuum and the atmosphere was replaced with hydrogen (1 bar). After 12 h, the balloon was removed and the mixture was filtered through diatomaceous earth and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 180 mg (35%) of the title compound.

Workup

  1. customthe balloon was removed
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-affead8c28d54cfba81fec9a5e012833
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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