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

HRID 513405Notes

Reaction equation

HRID 513405 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.O.NN>[Ni].CO>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 964436-Methyl-8-nitroquinoline2×

Product 1

HCID 1102378-Quinolinamine, 6-methyl-Yield 62.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a similar fashion using route 6 general procedure 14, 6-methyl-8-nitroquinoline (Intermediate 42) (300 mg, 1.6 mmol), Raney nickel (60 mg, 20% wt) hydrazine hydrate (0.32 ml, 6.30 mmol) and MeOH (8 ml) gave the title compound (159 mg) which was used in the next step without purification.

Sources & evidence

ORD record
ord-235214a272a64df0a0d269575b62fd62
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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