Hydrazine hydrate (1:1) → 8-Quinolinamine, 5,6-dimethyl-

HRID 513406Notes

Reaction equation

HRID 513406 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.O.NN>[Ni].CO>[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1104645,6-Dimethyl-8-nitroquinoline2×

Product 1

HCID 1104658-Quinolinamine, 5,6-dimethyl-Yield 77.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a similar fashion using route 6 general procedure 14, 5,6-dimethyl-8-nitroquinoline (Intermediate 43) (200 mg, 0.9 mmol), Raney nickel (40 mg, 20 wt), hydrazine hydrate (200 μl, 3.9 mmol) and MeOH (5 ml) gave the title compound (120 mg, 77%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-d41896e8a9034dca90f93466886099c8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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