6-Nitroquinolin-5-ylamine → Quinoline-5,6-diamine

HRID 48213Notes

Reaction equation

HRID 48213 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2>C1COCC1.CO.[Ni]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 1

HCID 1189016-Nitroquinolin-5-ylamine

Product 1

HCID 426874Quinoline-5,6-diamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-amino-6-nitroquinoline (25 g, 0.13 mol) in THF (500 mL) and methanol (500 mL) was treated with Raney nickel (7 g) under a hydrogen atmosphere (50.4 psi) on a Parr apparatus for 3.4 hours. Standard work-up gave the 5,6-diaminoquinoline.

Sources & evidence

ORD record
ord-7254d1bc18134c949e814f0cd113c64c
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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