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

HRID 1093980Notes

Reaction equation

HRID 1093980 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-5910f439e53f4f2da91ba9f504a899e9
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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