HCID 22072743, compound → HCID 21481008, compound

HRID 1490326Notes

Reaction equation

HRID 1490326 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[C:17]([CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:21]=1[N+:30]([O-])=O)=O)(=[O:3])[CH3:2]>[Zn].C(O)(=O)C>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[C:17]1[NH:30][C:21]2[C:20]([CH:19]=1)=[CH:25][C:24]([O:26][CH3:27])=[C:23]([O:28][CH3:29])[CH:22]=2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 22072743HCID 22072743, compound

Product 1

HCID 21481008HCID 21481008, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a 80% acetic acid solution of 4.60 g of 2-(2-acetamidoethyl)-2'-nitro-4,4', 5,5'-tetramethoxydeoxybenzoin was slowly added 4.7 g of zinc at 85° C. The reaction mixture was filtered, washed with ethanol, and the solvent was evaporated. To the residue was added an ammonium hydroxide aqueous solution, and the mixture was extracted with ethyl acetate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate) to yield 1.84 g of the title compound.

Workup

  1. customat 85° C
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ethanol
  4. customthe solvent was evaporated
  5. additionTo the residue was added an ammonium hydroxide aqueous solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-36a6637f7235452d9170a6e7ff367d3b
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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