Malononitrile → HCID 57845531, compound

HRID 734644Notes

Reaction equation

HRID 734644 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[N+:6]([C:9]1[N:14]=[CH:13][C:12]([C:15](=O)[CH2:16][NH:17]C(=O)C)=[CH:11][CH:10]=1)([O-:8])=[O:7].[OH-].[K+]>CO>[NH2:4][C:3]1[NH:17][CH:16]=[C:15]([C:12]2[CH:13]=[N:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=2)[C:2]=1[C:1]#[N:5]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 14797Potassium HydroxideHCID 57845548HCID 57845548, compound

Product 1

HCID 57845531HCID 57845531, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

0.022 g (0.336 mmol) of malononitrile is added at a temperature in the region of 20° C., under an argon atmosphere, to 0.050 g (0.224 mmol) of N-[2-(6-nitropyridin-3-yl)-2-oxoethyl]acetamide in solution in 5 cm3 of methanol. The reaction medium is cooled to a temperature in the region of 0° C. and then 0.1 cm3 of a 50% aqueous potassium hydroxide solution is added. After stirring for 15 minutes at a temperature in the region of 20° C. and then for 1.15 hours at a temperature in the region of 65° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and then diluted in 50 cm3 of ethyl acetate. The organic phase is washed with 10 cm3 of water and 10 cm3 of a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.043 g of 2-amino-4-(6-nitropyridin-3-yl)-1H-pyrrole-3-carbonitrile in the form of a brown solid. ES+: m/z=230 (MH+).

Workup

  1. waitfor 1.15 hours at a temperature in the region of 65° C.
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. additiondiluted in 50 cm3 of ethyl acetate
  4. washThe organic phase is washed with 10 cm3 of water and 10 cm3 of a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-3a5bfd55b94f492d975a13ea1b2a69af
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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