Morpholine → 5-Morpholino-6-fluoro-8-nitroquinaldine

HRID 1583603Notes

Reaction equation

HRID 1583603 reaction equation
Br[C:2]1[C:11]([F:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:16])=[N:7]2.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CN(C=O)C>[O:20]1[CH2:21][CH2:22][N:17]([C:2]2[C:11]([F:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([CH3:16])=[N:7]3)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 131919625-Bromo-6-fluoro-8-nitroquinaldine

Product 1

HCID 202590075-Morpholino-6-fluoro-8-nitroquinaldineYield 35.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5-Bromo-6-fluoro-8-nitroquinaldine (9.0 g) and morpholine (13.7 g) were dissolved in 90 ml of DMF and the solution was stirred at an internal temperature of 70° C. for 6.5 hours. Excessive morpholine and DMF were distilled off under reduced pressure and n-hexane was added to the residue followed by sufficient stirring. Then, isopropanol was added to the solution to precipitate solids which then were collected by filtration. The solids were dissolved in water and the aqueous solution was rendered alkaline with an aqueous sodium hydroxide solution to precipitate solids, which were collected by filtration to give 3.3 g of 5-morpholino-6-fluoro-8-nitroquinaldine.

Workup

  1. distillationExcessive morpholine and DMF were distilled off under reduced pressure and n-hexane
  2. additionwas added to the residue
  3. additionThen, isopropanol was added to the solution
  4. customto precipitate solids which
  5. filtrationthen were collected by filtration
  6. dissolutionThe solids were dissolved in water
  7. customto precipitate solids, which
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d82a9b35e6e540649ed0d7dd5a2baaa6
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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