HCID 19027046, compound → HCID 19027055, compound

HRID 1090078Notes

Reaction equation

HRID 1090078 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-673dfd0c5980478995cd78bcb63e0a22
Source dataset
uspto-grants-1992_01
Patent number
US05081123

Reaction notes

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