Dimethylformamide → 6-Aminoquinoline-5-carbonitrile

HRID 591014Notes

Reaction equation

HRID 591014 reaction equation
[N+]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([O-])=O.[C:14](CC(OCC)=O)#[N:15].[OH-].[K+].C[N:25](C)C=O>>[NH2:25][C:9]1[CH:8]=[CH:7][C:6]2[N:5]=[CH:4][CH:13]=[CH:12][C:11]=2[C:10]=1[C:14]#[N:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7764Ethyl cyanoacetateHCID 14797Potassium HydroxideHCID 877592-Nitroquinoline

Product 1

HCID 15072406-Aminoquinoline-5-carbonitrileYield 70%

Procedure

Nitroquinoline (5 g, 28.71 mmol) was added to a stirred solution of ethyl cyanoacetate (9.74 g, 86.13 mmol) and potassium hydroxide (4.83 g, 86.13 mmol) in N,N-dimethylformamide (87 mL). The mixture was stirred at room temperature for 22 hours. Then the solvent was removed in vacuo and the residue was hydrolyzed with chlorohydric acid (10%) at reflux for 3 hours. The mixture was basified with sodium hydroxide (10%) and extracted three times with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/methanol 95/5) to give the desired product (16a) (3.4 g, 20.1 mmol, 70%).

Workup

  1. customThen the solvent was removed in vacuo
  2. temperatureat reflux for 3 hours
  3. extractionextracted three times with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-fd9032b2f50a41ec865b6bfa8354fbd1
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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