Methylamine → 4-Methylamino-3-nitroquinoline

HRID 1789430Notes

Reaction equation

HRID 1789430 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 139583214-Methylamino-3-nitroquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.7 g (0.030 mole) of 4-hydroxy-3-nitroquinoline in 50 ml of N,N-dimethylformamide was added 9.3 g (0.060 mole) of phosphorous 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-97b456bb57504bd59428925f2a296995
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

Loading…