Ammonia → 2-Chloro-3-nitroquinolin-4-amine

HRID 1292485

Reaction equation

HRID 1292485 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:16]>CO>[NH2:16][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[C:11]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 218980422-Chloro-3-nitroquinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

2,4-dichloro-3-nitroquinoline (5.3 g, 0.218 mol) was combined with 75 mL of 15 percent ammonia in methanol and the mixture was heated at about 45° C. for about 4 hours. The reaction mixture was cooled to room temperature, and the precipitated product was removed by filtration. The volume of methanol was reduced to about 35 mL, and the precipitated product was removed by filtration. The volume of methanol was then reduced to about 10 mL and the precipitated product was again removed by filtration. The combined solids were stirred in aqueous sodium bicarbonate, filtered, and dried to afford a solid product 4-amino-2-chloro-3-nitroquinoline.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe precipitated product was removed by filtration
  3. customthe precipitated product was removed by filtration
  4. customthe precipitated product was again removed by filtration
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-f6a1c53dd5534e4ca0bdbe6a80ac5547
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Linked notes

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