Hydrazine hydrate (1:1) → 2-Chloroquinolin-8-amine

HRID 513380Notes

Reaction equation

HRID 513380 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-])=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.NN>[Ni].CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 3194532-Chloro-8-nitroquinoline2×

Product 1

HCID 3465192-Chloroquinolin-8-amineYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In the similar fashion using route 6 general procedure 14, 2-chloro-8-nitroquinoline (Intermediate 24) (100 mg, 0.48 mmol), Raney nickel (20 mg, 20% wt), hydrazine hydrate (96 mg, 1.92 mmol) and MeOH (10 ml) gave the crude title compound (70 mg, 82%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-71d4cc4850ba47518f19eedc5e69d5a4
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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