Sodium Cyanide → Ethyl 4-(cyanomethyl)-1H-pyrrole-2-carboxylate

HRID 241715Notes

Reaction equation

HRID 241715 reaction equation
[I-].[CH2:2]([O:4][C:5]([C:7]1[NH:11][CH:10]=[C:9]([CH2:12][N+](C)(C)C)[CH:8]=1)=[O:6])[CH3:3].[C-:17]#[N:18].[Na+]>C(O)C>[C:17]([CH2:12][C:9]1[CH:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[NH:11][CH:10]=1)#[N:18]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86662429[5-(Ethoxycarbonyl)-1H-pyrrol-3-yl]-N,N,N-trimethyl-methanaminium iodide

Product 1

HCID 66636709Ethyl 4-(cyanomethyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product obtained in Step E and sodium cyanide (0.225 g) in ethanol is heated at reflux for 72 hours. After evaporation to dryness, the residue is taken up in a mixture of CH2Cl2/water. The aqueous phase is extracted three times with CH2Cl2. The organic phases are combined. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness to yield the title product which is used directly in the next Step.

Workup

  1. temperatureat reflux for 72 hours
  2. customAfter evaporation to dryness
  3. additionthe residue is taken up in a mixture of CH2Cl2/water
  4. extractionThe aqueous phase is extracted three times with CH2Cl2
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-dc555aa76ab04acf8ca88d501acdb85b
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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