Hydrazine hydrate (1:1) → 5-Chloro-6-fluoroquinolin-8-amine

HRID 513404Notes

Reaction equation

HRID 513404 reaction equation
[Cl:1][C:2]1[C:11]([F: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>[Cl:1][C:2]1[C:11]([F: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 681829415-Chloro-6-fluoro-8-nitroquinoline2×

Product 1

HCID 681830075-Chloro-6-fluoroquinolin-8-amineYield 49.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a similar fashion using route 6 general procedure 14, 5-chloro-6-fluoro-8-nitroquinoline (Intermediate 41) (300 mg, 1.34 mmol), Raney nickel (60 mg, 20% wt), hydrazine hydrate (270 mg, 5.40 mmol) and MeOH (5 ml) gave the title compound (130 mg, 49%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-2e626f18667b4ad7b1db1f5f5082abf8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…