Methylamine → 4-Methylamino-3-nitroquinoline

HRID 1789414Notes

Reaction equation

HRID 1789414 reaction equation
[CH3:1][NH2:2].Cl[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]>O>[CH3:1][NH:2][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 139583214-Methylamino-3-nitroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 40% aqueous methylamine was added, in small portions, 30.Og (0.144 mole) of 4-chloro-3-nitroquinoline. The reaction mixture was heated at its reflux temperature for about 0.75 hour. After cooling, the mixture was poured into 300 ml of water. The solid was separated by filtration, and was then suspended in 300 ml of water. Acidification with 6N hydrochloric acid to pH 3 to 4 effected dissolution of most of the solid. Filtration was followed by basification of the filtrate with concentrated ammonium hydroxide to pH 8 to 10 to provide a yellow precipitate. The solid was separated by filtration, washed with water, and recrystallized from ethanol to provide yellow 4-methylamino-3-nitroquinoline, m.p. 168-170° C. Analysis: Calculated for C10H9N3O2 %C, 59.1; %H, 4.5: %N, 20.7: Found: %C, 59.0; %H, 4.2; %N, 20.8.

Workup

  1. temperatureThe reaction mixture was heated at its
  2. temperaturereflux temperature for about 0.75 hour
  3. temperatureAfter cooling
  4. customThe solid was separated by filtration
  5. dissolutiondissolution of most of the solid
  6. filtrationFiltration
  7. customto provide a yellow precipitate
  8. customThe solid was separated by filtration
  9. washwashed with water
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-701fcea6be6145faa217161bfc2ee4fd
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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