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

HRID 415498

Reaction equation

HRID 415498 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 (3) of Reaction Scheme II, a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula XXIX is reduced to provide a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XXX. 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, isopropanol, ethyl acetate, or acetonitrile. The reaction can be carried out at ambient temperature.

Workup

  1. customIn step (3) of Reaction Scheme II

Sources & evidence

ORD record
ord-092e7878e01d4e2399ea130119ce7f3e
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Linked notes

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