Methylamine → N-Methyl-3-nitro-4-quinolinamine

HRID 255551Notes

Reaction equation

HRID 255551 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].P(Cl)(Cl)(Cl)=O.[CH3:20][NH2:21]>CN(C)C=O.O>[CH3:20][NH:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 24813Phosphorus oxychlorideHCID 178526762HCID 178526762, compound

Product 1

HCID 13958321N-Methyl-3-nitro-4-quinolinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.7 g (0.30 mole) of 4-hydroxy-3-nitroquinoline in 50 ml of N,N-dimethylformamide was added 9.3 g (0.60 mole) of phosphorus oxychloride. The solution was heated on a steam bath for 5 minutes, then poured with stirring into 200 ml of 40% aqueous methylamine. The mixture was heated on a steam bath for fifteen minutes, then diluted with 200 ml of water. The solid was separated by filtration, then dissolved in dilute hydrochloric acid. The solution was filtered and the filtrate was basified with ammonium hydroxide. The solid precipitate was separated by filtration, washed with water and dried to provide Yellow solid 4-methylamino-3-nitroquinoline, m.p. 167°-171° C.

Workup

  1. temperatureThe solution was heated on a steam bath for 5 minutes
  2. additionpoured
  3. temperatureThe mixture was heated on a steam bath for fifteen minutes
  4. customThe solid was separated by filtration
  5. dissolutiondissolved in dilute hydrochloric acid
  6. filtrationThe solution was filtered
  7. customThe solid precipitate was separated by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-c145f8bf51c94545999de9c06ba1dd10
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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