Ethyl Acetate → HCID 68276419, compound

HRID 1048771Notes

Reaction equation

HRID 1048771 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([F:21])[CH:20]=1)[NH2:17].C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:15]=[C:16]([NH:17][C:2]2[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=2)[CH:18]=[C:19]([F:21])[CH:20]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 965953,5-DifluoroanilineHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 68276419HCID 68276419, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6.5 g of 6-chloro-3-nitropicolinonitrile (0.065 mol) and 6.2 g of 3,5-difluoroaniline (0.048 mol) in 100 ml of toluene is heated at 70° C. for 5 hours. The crude reaction product is diluted in an ethyl acetate fraction and washed using saturated NaCl solution. The organic phase is dried with sodium sulfate and the residue purified by silica gel chromatography (AcOEt/petroleum ether) to yield 3.9 g (33%) of a yellow solid.

Workup

  1. customThe crude reaction product
  2. washwashed
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. customthe residue purified by silica gel chromatography (AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-87658ed71d6c46ef847d34f562ee00b9
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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