Sodium Hydroxide → 5-Morpholino-6-fluoro-8-aminoquinaldine

HRID 434673Notes

Reaction equation

HRID 434673 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[CH:15][C:14]([N+:18]([O-])=O)=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]([CH3:21])=[N:12]3)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)(=O)C.Cl.O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[CH:15][C:14]([NH2:18])=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11]([CH3:21])=[N:12]3)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 202590075-Morpholino-6-fluoro-8-nitroquinaldine

Product 1

HCID 202589995-Morpholino-6-fluoro-8-aminoquinaldineYield 80.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Stannous chloride dihydrate (5.7 g) was added to a solution of 1.8 g of 5-morpholino-6-fluoro-8-nitroquinaldine in 30 ml of acetic acid and 20 ml of concentrated hydrochloric acid was added dropwise to the mixture with stirring. After completion of addition the mixture was stirred at room temperature for 1 hour, diluted with water and rendered alkaline with an aqueous sodium hydroxide solution to form precipitations, which then were extracted with dichloromethane, after drying over magnesium sulfate the solvent was distilled off to give 1.30 g of 5-morpholino-6-fluoro-8-aminoquinaldine.

Workup

  1. additionwas added dropwise to the mixture
  2. additionAfter completion of addition the mixture
  3. stirringwas stirred at room temperature for 1 hour
  4. customto form
  5. customprecipitations, which
  6. extractionthen were extracted with dichloromethane
  7. dry with materialafter drying over magnesium sulfate the solvent
  8. distillationwas distilled off

Sources & evidence

ORD record
ord-b0787009cebd4fa792d1173002c2c714
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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