Hydrazine hydrate (1:1) → N6-methylquinoxaline-5,6-diamine

HRID 1772009Notes

Reaction equation

HRID 1772009 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([N+:13]([O-])=O)=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[N:6]2.O.NN>CO.[Ni]>[CH3:1][NH:2][C:3]1[C:4]([NH2:13])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[N:6]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 34917146-METHYLAMINO-5-NITROQUINOXALINE

Product 1

HCID 4121983N6-methylquinoxaline-5,6-diamineYield 102.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-methyl-5-nitroquinoxaline-6-amine (1.3 g, 6.4 mmol) in MeOH (100 mL) was added hydrazine hydrate (1.27 g, 25.5 mmol) and Raney Ni (0.2 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 N6-methylquinoxaline-5,6-diamine as a black solid (1.14 g, yield 100%). ESI MS: m/z 175.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-d0c204b4b2794436832f4bb5c30f6dcb
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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