3-Nitroquinolin-4-amine → HCID 178419901, compound

HRID 1663420Notes

Reaction equation

HRID 1663420 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+]([C:18]1C=NC2C(C=1N)=NC=CC=2)([O-])=O.N1C2C(=CC=CC=2)C(N)=C(N)[CH:30]=1.[N:41]1[C:50]2[C:45](=[N:46][CH:47]=[CH:48][CH:49]=2)[C:44]([NH2:51])=[C:43]([NH2:52])[CH:42]=1>>[NH:14]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=[CH:18]1.[NH:51]1[C:44]2[C:45]3[N:46]=[CH:47][CH:48]=[CH:49][C:50]=3[N:41]=[CH:42][C:43]=2[N:52]=[CH:30]1

Participants

6

Reactant 4

HCID 2800053-Nitroquinolin-4-amineHCID 15142893,4-DiaminoquinolineHCID 131227883-Nitro-1,5-naphthyridin-4-amineHCID 22172703[1,5]Naphthyridine-3,4-diamine

Product 2

HCID 178419901HCID 178419901, compoundHCID 1784207351h-Imidazo[4,5-c][1,5]naphthyridine

Procedure

In steps (2) and (3) of Reaction Scheme III, a 3-nitroquinolin-4-amine or 3-nitro[1,5]naphthyridin-4-amine of Formula XLI is first reduced to a quinoline-3,4-diamine or [1,5]naphthyridine-3,4-diamine of Formula XLII, which is then treated with a halogen-substituted carboxylic acid equivalent to provide a 1H-imidazo[4,5-c]quinoline or 1H-imidazo[4,5-c][1,5]naphthyridine of Formula XLIII. Steps (2) and (3) of Reaction Scheme III can be carried out according to the methods described in steps (2) and (3) of Reaction Scheme I.

Sources & evidence

ORD record
ord-d2c52330e7fd4bb2ad36c60382e563ef
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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