Water → HCID 23369746, compound

HRID 1900732Notes

Reaction equation

HRID 1900732 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH2:5]1)[NH:12][C:11](=[O:17])[CH:10]=[CH:9]3.[C-:19]#[N:20].[K+].O>CN(C)C=O>[C:19]([CH2:2][CH2:3][CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH2:5]1)[NH:12][C:11](=[O:17])[CH:10]=[CH:9]3)#[N:20]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 23369691HCID 23369691, compound

Product 1

HCID 23369746HCID 23369746, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-(2-Chloroethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.5 g) was dissolved in dimethylformamide (50 ml). To the solution, potassium cyanide (2.0 g) was added and stirred at 100° C. for three hours. After the reaction was completed, the reaction liquid was condensed under reduced pressure. Water was added thereto and extraction was performed with chloroform. The chloroform phase was dried and condensed under reduced pressure. The residue was recrystallized from a solvent mixture of chloroform-ether to obtain 1.4 g of 2-(2-cyanoethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as pale yellow prisms (96.8%).

Workup

  1. customthe reaction liquid
  2. customcondensed under reduced pressure
  3. extractionextraction
  4. dry with materialThe chloroform phase was dried
  5. customcondensed under reduced pressure
  6. customThe residue was recrystallized from a solvent mixture of chloroform-ether

Sources & evidence

ORD record
ord-7ca6042584f344bd92da9e82eaaa0830
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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