Ethanol → HCID 18979044, compound

HRID 1901474Notes

Reaction equation

HRID 1901474 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[C:8]([CH3:17])[CH:9]=[C:10]([N+:14]([O-])=O)[C:11]=2[CH3:13])[N:6]=[CH:5][CH:4]=1)#[N:2].C(O)C.[OH-].[Na+]>O>[NH2:14][C:10]1[C:11]([CH3:13])=[C:12]2[C:7](=[C:8]([CH3:17])[CH:9]=1)[N:6]=[CH:5][CH:4]=[C:3]2[C:1]#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 10727993HCID 10727993, compound

Product 1

HCID 18979044HCID 18979044, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-cyano-5,8-dimethyl-6-nitroquinoline (2.54 g, 11.2 mmol), stannous chloride dihydrate (12.6 g, 55.9 mmol) and ethanol (200 mL) is heated at 60° C. for 1.5 hours. The reaction is cooled to room temperature, and water (60 mL) is added. The mixture is basified with 10% aqueous sodium hydroxide solution (70 mL) and subsequently extracted with methylene chloride (3×150 mL). Drying (sodium sulfate) and evaporation provides 6-amino-4-cyano-5,8-dimethylquinoline.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionsubsequently extracted with methylene chloride (3×150 mL)
  3. customDrying
  4. custom(sodium sulfate) and evaporation

Sources & evidence

ORD record
ord-d4d8df49b8bc47fe9725f06d7d3537f7
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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