Ethanol → HCID 54108053, compound

HRID 1598653Notes

Reaction equation

HRID 1598653 reaction equation
[CH3:1][C:2]1[C:11]([N+]([O-])=O)=[CH:10][C:9]([CH3:15])=[C:8]2[C:3]=1[C:4]([O:16][CH3:17])=[CH:5][CH:6]=[N:7]2.C(O)C.[OH-].[NH4+:22]>O>[NH2:22][C:4]1([O:16][CH3:17])[C:3]2[C:8](=[C:9]([CH3:15])[CH:10]=[CH:11][C:2]=2[CH3:1])[N:7]=[CH:6][CH2:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 105615364-Methoxy-5,8-dimethyl-6-nitroquinoline

Product 1

HCID 54108053HCID 54108053, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask is placed 5,8-dimethyl-4-methoxy-6-nitroquinoline (1.16 g, 5.0 mmol) with stannous chloride dihydrate (5.64 g, 25 mmol) and ethanol (50 mL). The mixture is refluxed for 1 hour, diluted with water (100 mL) and concentrated ammonium hydroxide (30 mL), and extracted with chloroform (2×200 mL). The organic portion is dried over potassium carbonate, filtered and the solvents removed by rotary evaporation, yielding 4-amino-5,8-dimethyl-4-methoxyquinoline.

Workup

  1. customIn a flask is placed
  2. temperatureThe mixture is refluxed for 1 hour
  3. extractionextracted with chloroform (2×200 mL)
  4. dry with materialThe organic portion is dried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-f818d798c6ca4e95893945366d66f3d3
Source dataset
uspto-grants-1998_04
Patent number
US05739148

Reaction notes

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