HCID 19027046, compound → HCID 19027055, compound

HRID 465310Notes

Reaction equation

HRID 465310 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13]([C:15](OCC)=[O:16])=[O:14])=[C:4]([N+:20]([O-:22])=O)[CH:3]=1.[H][H]>CN(C)C=O.[Ni]>[Br:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[NH:12][C:13](=[O:14])[C:15](=[O:16])[N:20]([OH:22])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 19027046HCID 19027046, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19027055HCID 19027055, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-1-ethoxalylamino-2-nitronaphthalene (0.20 g, 0.5 mmol) in 20 ml of N,N-dimethylformamide was hydrogenated at room temperature and atmospheric pressure in the presence of a small amount of Raney-Ni. After the hydrogen uptake was complete, the mixture was filtered. The filtrate was evaporated to dryness and the residue was triturated with water and hot ethanol to give 100 mg (62%) of the title compound. M.p. >200° C. dec.; IR (KBr): 1690 cm-1 ; MS (m/e): 306 (M+, 2%), 308 ((M+2)+, 2%).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was triturated with water and hot ethanol

Sources & evidence

ORD record
ord-f26beb4c93364187b0641a302130cf28
Source dataset
uspto-grants-1992_10
Patent number
US05153195

Reaction notes

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