4,5-Dibromo-2-nitroaniline → 4,5-Dibromobenzene-1,2-diamine

HRID 444441Notes

Reaction equation

HRID 444441 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:6]([N+:10]([O-])=O)=[CH:7][C:8]=1[Br:9])[NH2:5]>C(O)C.[Ni]>[Br:1][C:2]1[C:8]([Br:9])=[CH:7][C:6]([NH2:10])=[C:4]([NH2:5])[CH:3]=1

Participants

4

Reactant 1

HCID 127110274,5-Dibromo-2-nitroaniline

Product 1

HCID 121969444,5-Dibromobenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Following the procedure of Example 9, 5 g. of 3,4-dibromo-6-nitroaniline were reduced in anhydrous ethanol with Raney nickel to yield 4,5-dibromo-o-phenylenediamine which was not isolated but mixed immediately with 2.47 g. of 2-ketoglutaric acid. One hundred ml. of ethanol were added and the mixture heated to refluxing temperature for 3 hours. 3 gms. of β-(6,7-dibromo-3,4-dihydro-3-oxo-2-quinoxaline)propionic acid were obtained melting at 249°-250° C. The free acid was converted to the corresponding ethyl ester by the procedure of Example 8. Ethyl β-(6,7-dibromo-3,4-dihydro-3-oxo-2-quinoxaline)propionate thus prepared melted at 189°-190° C.

Sources & evidence

ORD record
ord-7469d21f301142f0a68050d14ebfbf7b
Source dataset
uspto-grants-1981_04
Patent number
US04264600

Reaction notes

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