Ammonia → HCID 9881674, compound

HRID 353223Notes

Reaction equation

HRID 353223 reaction equation
[NH3:1].Cl[C:3]1[C:8]([C:9]#[N:10])=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:5]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:4]=1>C(O)C>[NH2:1][C:3]1[C:8]([C:9]#[N:10])=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:5]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:4]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 12992133HCID 12992133, compound

Product 1

HCID 9881674HCID 9881674, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of ammonia in ethanol, 30 ml, (ethanol saturated at 0° C. with an ammonia gas) was added to 2-chloro-6-(2-furyl)-5-(4-pyridyl)-3-pyridinecarbonitrile (200 mg, 0.710 mmol). Then, it was sealed in a stainless steel autoclave, and heated under stirring at 100° C. After 24 hours, the reaction solution was cooled as it was and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=2:1, 1:1, 1:2), and then suspended in diethyl ether. The resulting precipitates were collected by filtration and washed with diethyl ether, to give the title compound (50 mg, 27%) as a pale orange solid.

Workup

  1. temperatureheated
  2. temperaturethe reaction solution was cooled as it
  3. concentrationconcentrated
  4. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=2:1, 1:1, 1:2)
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-d0160555cb2943f7ab31c2875aa49b73
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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