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

HRID 520272

Reaction equation

HRID 520272 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>C(O)C.[Pd]>[NH2:1][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

Participants

4

Reactant 1

HCID 2800053-Nitroquinolin-4-amine

Product 1

HCID 15142893,4-Diaminoquinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 8 was prepared as described elsewhere [Van Galen, P. J. M. et. al. (1991) ibid.]. In brief, to a mixture of 3-nitro-4-aminoquinoline 7 (3.2 g, 20 mmol) in absolute ethanol (60 ml) was added 10% palladium on charcoal (0.17 g). The mixture was hydrogenated under 2.5-3.5 atm pressure till the product was formed and subsequently filtered over Hyflo. The filtrate was evaporated and the residue was gradually solidified and dried in vacuum. Yield: 2.66 g (98%). Mp.: 183-185° C. MS (ESI) m/z 161.0 (M+1)+. 1H NMR (DMSO-d6): δ 4.73 (broad s, 2H, NH2); 5.88 (s, 2H, NH2); 7.16-7.37 (m, 2H, Ar); 7.64-7.70 (m, 1H, Ar); 7.98-8.03 (m, 1H, Ar); 8.22 (s, 1H, Ar).

Workup

  1. customwas formed
  2. filtrationsubsequently filtered over Hyflo
  3. customThe filtrate was evaporated
  4. customdried in vacuum

Sources & evidence

ORD record
ord-f9551806eb7c4743882b19dbd508781e
Source dataset
uspto-grants-2016_05
Patent number
US09326978B2

Linked notes

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