Hydrazine hydrate (1:1) → 6-Quinoxalinamine

HRID 1772005Notes

Reaction equation

HRID 1772005 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[N:7]2)([O-])=O.O.NN>CO.[Ni]>[N:10]1[C:11]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:13][CH:12]=2)[N:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 96029Quinoxaline, 6-nitro-

Product 1

HCID 2378596-QuinoxalinamineYield 99.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-nitroquinoxaline (17.0 g, 0.097 mol) in MeOH (500 mL) was added hydrazine hydrate (19.4 g, 0.39 mol) and Raney Ni (2.0 g). The mixture was stirred at room temperature for 1 h. The mixture was then filtered, and the filtrate was concentrated under reduce pressure to give quinoxalin-6-amine as a yellow solid (14.0 g, yield 99%). ESI MS: m/z 146.1 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-17f67d3c6ba94ce7b8335d3fcc90b57f
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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