5-Cyanoquinoline → HCID 86093121, compound

HRID 1294705Notes

Reaction equation

HRID 1294705 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N:13]#[C:14][NH2:15].[Na]>C(O)C>[C:14]([N:15]=[C:11]([C:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:10]=2[CH:9]=[CH:8][CH:7]=1)[NH2:12])#[N:13]

Participants

4

Reactant 2

HCID 47150285-CyanoquinolineHCID 57375518Cyanamidnatrium

Product 1

HCID 86093121HCID 86093121, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 24A (750 mg, 4.81 mmol) and sodium cyanamide (312 mg, 4.81 mmol) in ethanol (10 mL) was heated at reflux for 10 hours and cooled to ambient temperature. The solvent was removed under reduced pressure and the crude mixture was purified by silica gel chromatography, eluting with a gradient of 0-6% of methanol/methylene chloride to provide 0.3 g of the title compound. MS (ESI+) m/z 197 (M+H)+.

Workup

  1. temperatureat reflux for 10 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe crude mixture was purified by silica gel chromatography
  4. washeluting with a gradient of 0-6% of methanol/methylene chloride

Sources & evidence

ORD record
ord-cf4e99d31fed4391abb990d80c0632d8
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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