Hydrochloric Acid → HCID 19777516, compound

HRID 1381055Notes

Reaction equation

HRID 1381055 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:7]([NH2:9])=[O:8])([O-])=O.[H][H].[ClH:18]>O.[Pd]>[ClH:18].[ClH:18].[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([NH2:13])[CH:12]=1)[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 45113,5-DinitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 19777516HCID 19777516, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

3,5-Dinitrobenzamide (XIX) (85.0 g, 402 mMoles, Aldrich) was added to a suspension of 10% Pd/C (8.5 g) in concentrated HCl (74 ml) and water (730 ml). The mixture was hydrogenated at about 60 psi in a Parr hydrogenation apparatus until hydrogen was no longer being consumed (3 hours). TLC (silica, 80 chloroform/20 methanol) indicated that no starting material remained, and that to a single product with an Rf of 0.23 had occurred. The solution, which contained the product (XIX), was then filtered through a celite pack, the pack was washed with 300 ml water, and the filtrate and washings combined and used for the subsequent iodination.

Workup

  1. customwas no longer being consumed (3 hours)
  2. filtrationwas then filtered through a celite pack
  3. washthe pack was washed with 300 ml water

Sources & evidence

ORD record
ord-96bd214c0fb24b01b7d02c3a78f8c6e4
Source dataset
uspto-grants-1986_04
Patent number
US04584401

Reaction notes

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