3-Nitroquinolin-4-amine → 3,4-Diaminoquinoline

HRID 419283

Reaction equation

HRID 419283 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[N+:15]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[NH2:28])=[N:25][CH:24]=[CH:23][CH:22]=2)([O-])=O>>[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]([NH2:14])=[C:4]([NH2:1])[CH:5]=1.[N:20]1[C:21]2[C:26](=[N:25][CH:24]=[CH:23][CH:22]=2)[C:27]([NH2:28])=[C:18]([NH2:15])[CH:19]=1

Participants

4

Reactant 2

HCID 2800053-Nitroquinolin-4-amineHCID 131227883-Nitro-1,5-naphthyridin-4-amine

Product 2

HCID 15142893,4-DiaminoquinolineHCID 22172703[1,5]Naphthyridine-3,4-diamine

Procedure

In step (7) of Reaction Scheme I, a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula XXI is reduced to provide a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XXII. The reaction can be carried out by hydrogenation using a heterogeneous hydrogenation catalyst such as platinum on carbon. The hydrogenation is conveniently carried out in a Parr apparatus in a suitable solvent such as toluene, methanol, or acetonitrile. The reaction can be carried out at ambient temperature, and the product can be isolated using conventional methods.

Workup

  1. customIn step (7) of Reaction Scheme I

Sources & evidence

ORD record
ord-80e8be8d054246e083f54ace077cfcb4
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Linked notes

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