HCID 19990415, compound → HCID 19990426, compound

HRID 346153Notes

Reaction equation

HRID 346153 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11](OCC)=[O:12])=[O:10])=[C:4]([N+:16]([O-:18])=O)[CH:3]=1>CN(C)C=O.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:8][C:9](=[O:10])[C:11](=[O:12])[N:16]2[OH:18])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 19990415HCID 19990415, compound

Product 1

HCID 19990426HCID 19990426, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-1-ethoxalylamino-2-nitrobenzene (1.0 g, 3.2 mmol) in 50 ml of N,N-dimethylformamide was hydrogenated at atmospheric pressure and room temperature in the presence of a small amount of Raney-Ni. The catalyst was removed by filtration, and the filtrate was evaporated to dryness. The residue was tritureted with ethanol affording 0.68 g (84%) of the title compound. M.p.>250° C. dec.; 1H-NMR (DMSO-d6): 6.98-7.63 (m. 3H ArH) appr. 11.9 (very broad s 1H NH): IR (KBr): 1700 cm-1 ; MS (m/e): 256 (M+, 62%), 258 (M+2)+, 58%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ece344cbcabc485eb7c8becbcd718b1f
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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