Dimethylformamide → HCID 10727993, compound

HRID 1901473Notes

Reaction equation

HRID 1901473 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([CH3:16])[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=2[CH3:12])[N:5]=[CH:4][CH:3]=1.[CH3:17][N:18](C)C=O>O>[C:17]([C:2]1[C:11]2[C:6](=[C:7]([CH3:16])[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=2[CH3:12])[N:5]=[CH:4][CH:3]=1)#[N:18]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 10493059HCID 10493059, compound

Product 1

HCID 10727993HCID 10727993, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-5,8-dimethyl-6-nitroquinoline (3.87 g, 13.77 mmol), cuprous cyanide (3.67 g, 41.31 mmol) and dimethylformamide (70 mL) is stirred at room temperature for 30 minutes and then heated to 155° C. and stirred at this temperature for 1 hour. Water is added, and the reaction mixture is filtered. The precipitate is washed with water and methylene chloride. The filtrate is extracted with methylene chloride (3×125 mL), and the combined organic layers are dried (sodium sulfate) and evaporated. Purification by chromatography through a short column consisting of layers of sand/flash silica gel/sand, using chloroform as eluent, provides 4-cyano-5,8-dimethyl-6-nitroquinoline.

Workup

  1. temperatureheated to 155° C.
  2. stirringstirred at this temperature for 1 hour
  3. filtrationthe reaction mixture is filtered
  4. washThe precipitate is washed with water and methylene chloride
  5. extractionThe filtrate is extracted with methylene chloride (3×125 mL)
  6. dry with materialthe combined organic layers are dried (sodium sulfate)
  7. customevaporated
  8. customPurification by chromatography through a short column

Sources & evidence

ORD record
ord-237d50d586ca46caa3cb658e5e86e342
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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