Hydrazine hydrate (1:1) → 5-Chloroquinolin-8-amine

HRID 513381Notes

Reaction equation

HRID 513381 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.O.NN>[Ni].CO.C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[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 2427555-Chloro-8-nitroquinoline2×

Product 1

HCID 2248605-Chloroquinolin-8-amineYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In the similar fashion using route 6 general procedure 14, 5-chloro-8-nitroquinoline (Intermediate 25) (500 mg, 2.40 mmol), Raney nickel (100 mg, 20% wt), hydrazine hydrate (0.5 ml, 9.62 mmol) and MeOH/THF (10 ml, 4:1), gave the title compound (420 mg, 98%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-e36d20ac99d24f3eadf9e34ba0fd878a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…