Ammonia → 3-Nitroquinolin-4-amine

HRID 520271Notes

Reaction equation

HRID 520271 reaction equation
[NH3:1].[N+:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][CH:9]=2)([O-:4])=[O:3]>C1(C)C=CC=CC=1.C(O)CC>[N+:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH2:1])=[CH:12][CH:11]=[CH:10][CH:9]=2)([O-:4])=[O:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 2800053-Nitroquinolin-4-amine

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Compound 7 was prepared as described elsewhere [Van Galen, P. J. M. et. al. (1991) ibid.]. In brief, ammonia gas was passed, while stirring, through a solution of 3-nitro-4-chloroquinoline 6 (7.0 g, 30 mmol) in toluene (95 ml) and propanol (15 ml) till the product was formed. During the course of the reaction, the temperature was gradually raised till 70° C. After cooling, the solid was separated by filtration and washed successfully with toluene/2-propanol (70:30), ether and cold water until Cl− could no longer be detected. The solid was filtered off and dried at 80° C. Yield: 6.1 g (95%). Mp.: 255-257° C. 1H NMR (DMSO-d6): δ 7.50-7.66 (m, 1H, Ar); 7.81-7.92 (m, 2H, Ar); 8.59 (d, 1H, J=8.0 Hz, Ar); 9.03 (broad s, 2H, NH2); 9.18 (s, 1H, Ar)

Workup

  1. customwas formed
  2. customDuring the course of the reaction
  3. temperatureAfter cooling
  4. customthe solid was separated by filtration
  5. washwashed successfully with toluene/2-propanol (70:30), ether and cold water until Cl−
  6. filtrationThe solid was filtered off
  7. customdried at 80° C

Sources & evidence

ORD record
ord-9ff76148eb4d465181f0b2dfcfe1c3fb
Source dataset
uspto-grants-2016_05
Patent number
US09326978B2

Reaction notes

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